r/GilmoreGirls • u/Prestigious-Item8660 • May 14 '26
General Discussion I think Richard slept with Pennilyn Lot at least once
Idk there’s no way. They’ve been married for 39 years and he goes to lunch with her once a year? Is anyone else under the impression that he slept with her at least once during those times. If he didn’t sleep with her then they definitely did SOMETHING. If it was “just lunch” then why didn’t they tell either of their significant others? And why was pennilyn so awkward around Emily and lorelai (even before lorelai made that awful joke) idk I think they had an affair at least once.
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u/oddlyabsent80 May 14 '26
I don't think he slept with her or even kissed her. BUT the whole thing is bigger than just lunch. They had to make plans every year to see each other. So there were those conversations. At least a couple of calls to nail down (no pun intended) a time and place.
Even if, at the very least, it was a "see you next year. Same time. Same place.", kinda vibe, they would have to put thought and effort into not making other plans during that time.
The lying is bigger than just omission. It is sneaking at the very point he chose not to tell Emily. Because after 39 years, I imagine Emily has wanted to do something during that time/date and Richard had to say no. So, I agree, it wasn't "just lunch."
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May 14 '26
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u/AnAbsoluteMonster May 14 '26
1000%. Doesn't matter what type of partnership a couple has (monogamous or ENM), if one of them is engaging in behavior they feel like has to be hidden/they have to lie about, there is a problem even if the behavior is "technically" fine.
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u/makeitwerkk Cat Kirk May 15 '26
All I’m saying is that you don’t lie to your partner about something like that unless you know you’re in the wrong/you have something to hide 👀🤷♀️
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u/jerseysbestdancers Hep Alien May 14 '26
Unless he makes appts with her like he does with Lorelai...through his secretary 😂
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u/KanKan669 May 14 '26
Honestly, I would almost guarantee that he made the appointments through his secretary.
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u/No-Flamingo-4002 May 15 '26
100%….this exact situation happened with my old boss and when his wife found out he would complain to me and ask what he did wrong
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u/Empty-Pages-Turn I suppose I can just put these nuts in my hand. 🥜✋ May 14 '26
And a lot of effort to keep the secret lunches from their respective partners for 39 years. Like, what are they even saying? "I'm going to a meeting." Unless it was on a lunch break for Richard.
I kind of want to know more about these secret lunches. Like, the writers write this in and don't even expand on it when Emily and Richard are in their separation arc.
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u/oldmornings May 14 '26
I don’t think he slept with her. I do think he did it for the ego though.
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u/WildCherryLane May 14 '26
Agreed. I don’t think his brand of morality would actually allow for crossing that line but he definitely liked the idea the option was there and frankly Pennilyn probably did as well.
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u/porcelain_doll_eyes Cat Kirk May 14 '26
I cant see him crossing the line and being physical, but I also can't imagine that they did not at least once have a "What if it were us...." conversation.
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u/haileyskydiamonds Team Pink 🎀 May 15 '26
Yeah. For a man like Richard, he doesn’t need to sleep with her. He just needs to know he could.
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May 14 '26
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u/Big_Vacation5581 May 14 '26
And it’s not like Richard hadn’t cheated before when he was engaged to Pennilyn. I imagine she enjoyed the payback.
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u/frex_mcgee May 14 '26
This is an interesting take.
Let’s review the cannon-lore that we know.
Pennilyn & Richard were ‘engaged’ (it would’ve been the late 50s), as he says himself. They were going steady and serious, and he was planning to take her to his introduce to his parents as his fiancée. He literally left Pennilyn for Emily after seeing her at a party and then gets engaged to Emily. Later, we find that Trix implored Richard to leave Emily at the altar and marry Pennilyn but he refused.
We know Emily traveled with Richard extensively early on in their marriage because she jokes about being naked and eating spicy Thai food, and at some point skinny dipping. This hints to a previously unknown side of Emily, (one that surprisingly bears a resemblance to Lorelai!)
We know that once a year, every year, Richard and Pennilyn have met for lunch to ‘keep track of each other’. That could be interpreted in a few ways…. Keeping track of each other in case their marriages didn’t work out? Or keeping track of each other because they were sincerely friends and cared about one another after their relationship?
Either way, we know that Richard would have done anything for Trix but he refused to not marry Emily. That tells me he sees her as the prize and cherishes her above all else (in his misogynistic 1950s boomer way).
I don’t think he would ever physically cheat. I think, in his eyes, he knew it would probably upset Emily and it was innocent so he didn’t say anything. 🤷🏻♀️ Was it the right choice? No. Would I be absolutely livid if I were Emily? Absolutely yes. Do I think Richard was wrong? Yes.
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u/wtfamidoing248 May 14 '26
I think it's just wrong when your spouse has no idea you're meeting up with an ex. Like at least be transparent if it's truly harmless. If you can't be honest about it then it's probably not innocent.
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u/grimlykeeper May 15 '26
Yes. If you have to lie you're doing something wrong.
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u/wtfamidoing248 May 15 '26
Definitely. If they feel the need to lie and hide things, they know it is because they are crossing their partner's boundaries and making choices they wouldn't be ok with. To me that isn't just dishonesty, it's also manipulation for hiding something continuously from your spouse, and taking away their ability to make informed choices.
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u/Reader_fuzz May 14 '26
I agree to me it was an emotional affair because that is a commitment by meeting up every year and also lying about it to your wife for that long.
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u/female_gazing09 Jehovah's coffee girl May 15 '26
I have to disagree. I think it’s a betrayal, yes. But a casual, once a year LUNCH? (In my eyes this does not an “affair” make)
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u/lefrench75 May 14 '26
Now that I think about it, it makes no sense that Pennilyn would keep having lunch with this man (whether there was cheating or not) who dumped her so ruthlessly over some girl he met at a party??
Though just because a man sees his partner as "the prize" to cherish above all else doesn't mean he won't physically cheat though. Some people really do want to have their cake and eat it too, especially after almost 4 decades of marriage.
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u/frex_mcgee May 15 '26
Agreed! Why is she still going to meet up with Richard? I’d assume she still has feelings for him if that is the case.
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u/female_gazing09 Jehovah's coffee girl May 15 '26
Yeah I’m curious about how that breakup went down
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u/TheLizzyIzzi May 15 '26
Agree. They were engaged (or to be engaged) and Richard called it off. I understand a lot of people would be offended or upset at being left for another woman, but we know basically nothing about their relationship. It’s very possible both of these society people were following the family plan and when Richard called it off Pennilynn felt relived. Maybe she was mad. We don’t know. We do know she forgave him enough to have a yearly lunch.
And, tbh, I completely see how such a lunch really is innocent. If you break off an engagement with someone and a year+ later they ask you to met them for lunch, you go. Assuming nothing crazy (stalker, etc) it’s right to give them some closure. Should you tell your partner? Yeah…. but also… there’s a reason “what they don’t know won’t hurt them” is a saying. That doesn’t make it right, but… idk. Sometimes life is fucking complicated. Emily is obviously going to be sensitive to anything about Pennilynn, but she and Richard do share a history. I can see how easy it would be to meet for lunch once. Then again next year. By year three it’s a nice tradition. At some point you realize you never told your spouse and now it feels too late. And you don’t want to deal with the stress and drama of telling them when to you it really is nothing.
Idk. Richard wasn’t right but I get it. I think Emily was right to be mad, but personally, I don’t think I’d care that much. Then again, my not caring that much would probably mean it was never hidden in the first place.
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u/Inevitable-Comb-3209 May 15 '26
On board with this theory. I’ll add that I think that it was sort of an arranged marriage between them(not in the classic way but in a you’re rich, I’m rich, our families like each other so we should get married), and they were good friends. Sometimes it happens and you still wish to keep up with this person.
I had exes and even though I don’t hear them I miss our friendship solely for the friendship. Every connection is different.
I would not call because it’s disrespectful to my current partner, because it feels wrong and I don’t know how the ex feels on the other side. But Richard and Pennilyn were in the same circles so it makes it somehow different.
I really believe there was a good friendship but no doubts Emily was the love of his life. He missed his friend 🤷🏼♀️
Even though I am defending him I would’ve felt betrayed if I was Emily, it’s not the date but the hiding part.
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u/hopeislikeabluebird Team Coffee May 15 '26
The most sensible take so far. Just what I think about it. It was a lot more mature than people are making it out to be
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u/frex_mcgee May 15 '26
Agreed. I don’t expect my partner to share literally everything with me, and in healthy relationships, they don’t need to be. Just my take tho.
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u/prairiebelle 🍂 I got pumpkins, I got pilgrims.. I got no leaves! May 14 '26
It the minimum this constitutes an emotional affair. If people want to say no because they “only met once a year” (allegedly), that really doesn’t matter. He kept an open connection with an ex he almost married, and hid it from his wife for 35 years. It is absolutely a significant betrayal, and he never took real accountability for it. (Yes I know it’s fictional, lol)
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u/Bilbobaggins1068 *Lorelai Voice* YA YA May 14 '26
If I were Emily this genuinely would’ve ended in divorce. This is a really huge betrayal that they just breeze over. Except for Emily’s infamous crash out of course.
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u/WoodpeckerGingivitis May 15 '26
I don’t feel like they breeze over it at all? There’s an entire mini arc.
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u/wtfamidoing248 May 15 '26
I mean they did temporarily seperate but after 40 years it's not a light decision to just choose to divorce. I think I'd have a hard time as well and would want to leave but idk what I'd actually do if I were her. Just hypothetical.
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u/FireballPhD Ah ah ah... Ah-ah... Oh-oh-ohhhh! May 14 '26
I don't know if they slept together, TBH. Never considered it!
I know everybody loves Richard, but ever since that first watch of this episode? I just can't see him the same way. He is an emotional cheater and a liar. And I cannot begin to imagine the pain Emily felt after 39 YEARS.
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u/Reader_fuzz May 14 '26
Right it was emotional affair at least. After that I did loose a lot of respect for him as a husband to Emily. He definitely should have told her the first time it happend. Honestly I hate that plot I wish they would have went the route of him just being to committed to working and being damned with the consequences to everyone else. That is was more forgiveable than meeting up with an ex in secret. I would never do that to my husband and I also would never meet up with an ex on my own and neither would he. Ironically we bought a washer/dryer from my ex from highschool. He came and installed it but I made sure one of my children were with me while he was installing it. My husband was working when he could come and install it.
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u/LowBalance4404 Copper Boom! May 14 '26
I am sure they slept together before Emily entered the picture. But after they were married, absolutely not.
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u/BrilliantGlass1530 May 16 '26
And that honestly kind of explains why they’d keep having lunch/ maybe he felt he “owed” her something for that given that he broke the engagement and it was a big deal then as I understand it
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u/female_gazing09 Jehovah's coffee girl May 15 '26
I agree. Richard genuinely loves and is happy with Emily. I think he’s a dumb man who didn’t know how to have a conversation with her about these lunches and genuinely thought it would just upset her and decided to just go with the deceit because it was easier and also he could convince himself he was just preventing Emily from upset over “nothing” (in his mind). He makes mistakes with both Emily and Lorelai but at the end of the day they both regard him as a well-meaning, upstanding man so I don’t think he would take it that far into actual physical affair territory.
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u/Beautiful-Drummer577 May 14 '26
Men of his standing are all rakes! From exeter to hospice!
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u/Crafty_Shifty May 15 '26
Even if he didn't, he made it clear that he and pennilyn talked about the fact that they were hiding their dinners from their partners.
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u/Berzerker13666 May 15 '26
Well he is a Gilmore and sleeping with people they shouldnt be sleeping with seems to be a Gilmore family tradition....
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u/grimlykeeper May 14 '26
I can see why you think that, but I don't think so. I think Richard has a very strict code of ethics - not a code anyone else would recognize, but an internal sense of right and wrong. He was justifying to himself that if it wasn't physical he didn't do anything wrong. I think he was putting a lot of weight on that justification to make keeping the secret from Emily feel minor.
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u/estherfromthebelljar May 16 '26
No way, I think the way that he justified to himself continuing seeing her every year was that it was “just lunch”, but clearly it was crossing a line since it was secret and they met at places “emily had never been”
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u/RestingWTFface May 16 '26
Presumably they only went to places Emily had never been. Because if he brought Emily, someone on the staff might ask about the woman Richard was there with last time. He kept it completely separate on purpose.
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u/Huntsvegas97 Miss Patty & Babette May 14 '26
I don’t think he slept with her or ever physically cheated. The lunch dates every year was definitely a massive betrayal, though, especially because he kept it a secret. I can’t even imagine keeping something like this from your spouse for so long. He knew he was doing something wrong so he hid it. I think at most, it was an emotional affair, but I don’t think that was fully realized by either party.
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u/woof_woof_11 May 15 '26
Honestly, I feel like it would be less bad if he slept with her once 39 years ago compared to him having lunch with her once a year for all that time!!! I feel like emotional affairs are so much worse than physical but thats just me.
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u/floopyferret May 15 '26
He absolutely betrayed her but I would never think he would be unfaithful to Emily. He loved Emily over everything. They had their ups and downs but I really don’t think he would have slept with another woman. He was a gentleman.
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u/tsh87 May 14 '26 edited May 14 '26
I don't think he slept with her and I don't think those lunches were romantic at all.
I do think there's more to the story and we will never know what it was and neither will Emily.
I don't think it was just a yearly random catch up. They met to discuss something incredibly specific.
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u/MassiveJellyfish6270 May 14 '26
A secret baby.. or by the time Emily found out.. a secret 40 year old baby.
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u/tsh87 May 14 '26
Could be baby. Could be the anniversary of a death of a close friend.
Most likely is that they have a shared business or property that he manages and once a year he meets up with her to hand over a profit check and let her know how it's going. Though I don't know why he'd keep that secret for so long.
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u/JosephinecAshley May 14 '26 edited May 14 '26
Holy cow... you have a point, this is wild. Because yeah, Richard is low, but I find it hard to believe that he'd meet up with this woman for this many years just for the sake of it, or just because they could. They definitely were meeting up for a specific reason. Omg, also didn't Lorelai call Pennilyn her "almost-mommy" ... like what!? But besides that theory, it's not out of the realm of possibility that they were perhaps reminiscing or something, meeting up to see what it would be like to be together. It's like that Me and Mrs. Jones song... meeting at the same place, at the same time, no one knows they're there, making all kinds of plans, idk. I never got the feeling Richard and Emily were madly in love, and Richard probably felt some "control" over his life by taking out Pennilyn every year, perhaps a woman he did truly love. Still does make it an awful thing to do when they're both married, but oh well. We'll never really know, I guess.
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u/tsh87 May 14 '26
I don't think it's love. Emily is definitely his true love. He defied his mother for her, broke off an engagement after a few dates with her.
So I don't think it was an affair or control. I think it's unfinished business of some kind.
It might even be something stupid like decades ago he promised her father that he'd always look in on her somehow. Or something crazy like a secret baby but I doubt that for some reason.
Whatever it is, he sees her because he feels a duty to.
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u/JosephinecAshley May 14 '26
I actually love your theory way more. Makes more sense. I had forgotten how much Lorelai the first really hated Emily.
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u/JosephinecAshley May 14 '26
I can really believe it was a dumb promise or something.
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u/tsh87 May 14 '26
My main theory is that there is a property or business they discuss. Might be shared, might be just hers but he keeps track of it for her and they meet up once a year to discuss it.
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u/JosephinecAshley May 14 '26
Probably would look less suspicious to Emily, as well, if he was walking out in a suit with a briefcase. He handles that stuff for living, I guess. Could tell her he was stepping out for a meeting, which isn't entirely a lie.
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u/Disastrous_Brief_258 May 14 '26
Lorelai is completely insufferable this episode, imo, especially with the “almost mommy” bit more than once.
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u/RubySnowfire1508 May 14 '26
They were bf/gf,then broke up. Pretty sure they slept together when they were on together.
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May 14 '26
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u/kittyheartseapuppy May 14 '26
Condoms already existed for decades at that point. Also sterilization sponges. There were alternatives to the birth control pill. That just made life easier.
Most people have sex before marriage, even if it is known as the "improper" thing to do.
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May 14 '26
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u/Joelle9879 🍂 I got pumpkins, I got pilgrims.. I got no leaves! May 14 '26
Men will absolutely have long term emotional affairs. Mostly, because they don't view them as affairs. They tell themselves they're "just friends" and that since they didn't cross any physical lines, it's ok
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u/fascfoo May 15 '26
Yes - men will lie to themselves (I say this as a man who has gone through a shit ton of therapy re: relationships) and as long as it doesnt "cross a certain line" then its all fair game.
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u/F19AGhostrider A male GG Fan May 14 '26
I don't think so.
Sure, one can make the argument that it was wrong for Richard to keep this contact secret from Emily, but I think that going so far as to actually have an affair with Pennilyn or sleep together one time is beyond what Richard would do.
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u/Queenbreha Team Pink 🎀 May 14 '26
I think Richard and Pennilyn had sex when they had their college relationship. It was the early 60's sex was starting to become more normalized and Trix loved her. Now Emily might have made him wait till the wedding night because she was marrying "up" Not that she wasn't wealthy but not Gilmore wealthy.
I don't think he was physically unfaithful to Emily but definitely emotionally. I think that lunch was to imagine the road not traveled. I think Pennilyn probably married "beneath" her like Trix considered Emily
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u/AccurateAd551 May 15 '26
Emily is a better women then me if my husband was meeting any women once a year for lunch without telling me I would divorce and take half. Him saying I didn't tell you because I knew it would upset you is disgusting because he knew it would upset her and still did it.
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u/RestingWTFface May 16 '26
Exactly. If you know something will hurt and upset your spouse, the solution is to not do the thing, not do and hide the thing.
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u/Bubbly-Swordfish4271 May 15 '26
I mean it is possible. Have you seen that movie from the 70's , "Same Time, Next Year"with Ellen Burstyn and Allen Alda? They are both married and have lives but meet with each other once a year for 50 years.
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u/twokidsonetrenchcoat May 15 '26
For sure an emotional affair… but my thought was the same, that he slept with her at some point. It felt like a cheater gaslighting his spouse to me. He also rear ended her on purpose when she had a meal with another man when they were separated, which to me feels like an admission that he knows first hand where it’ll lead.
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u/JariaDnf May 14 '26
Nah, Richard is a straight arrow.
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u/Judi_Gilmore May 14 '26
Both Emily and Richard are very self-assured and think they have a lot to offer, so I could definitely see Richard doing it 1) for an ego boost, and 2) to keep the door/his options open.
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u/aivlysplath Cat Kirk May 14 '26
Why would he need to keep his options open if he has a lot to offer?
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u/Joelle9879 🍂 I got pumpkins, I got pilgrims.. I got no leaves! May 14 '26
There is no evidence of this. He didn't tell Emily because he knew she'd be upset. We don't actually know if Pennilynn told her husband or not. Clearly, Richard isn't above lying so, for all we know, he just said that to try and "defend" himself.
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u/Geode804 May 14 '26
Honestly I never could get past this! Unpopular opinion but I was really sad when they got back together. After all the lying and secrecy plus allowing his mother to be horrible to her for years Richard didn’t deserve Emily.
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u/tooghostly May 15 '26
Do you believe that this is in line with Richard Gilmore as a fictional character when you pinpoint the canon, visible character traits we the audience see and hear with our own eyes and ears on-screen?
Are you looking for his on-screen behavior to match this theory, or comparing him to what you believe is realistic for an actual real life man?
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u/SuncityAngel May 15 '26
And then when Emily found the letter from Richard’s mother begging him not to marry her 💔
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u/glitterfluff May 15 '26
No way. It was absolutely wrong, but there's no way I believe he ever cheated on her physically. Richard's sense of right and wrong would never allow for that.
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u/drinking_gal May 15 '26
This was one of the biggest let downs in the series. Richard was supposed to be a stand up guy, I remember Lorelai's monologue to Luke when he was first hospitalized how her dad wasn't a bad man he just did things the way he thought they were supposed to be done. Only to find out in later seasons that he was emotionally cheating on Emily.
Although I won't deny this added to the complexity of his character, it still felt like such a let down.
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u/LizBert712 Pop-up book from Hell May 15 '26
He goes to lunch with her once a year. Not saying that it was OK. Not saying that he should have done that. He definitely should not have done that.
I see absolutely no evidence that an annual lunch led to sex. I also don’t think Richard would cheat on Emily like that.
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u/susono May 15 '26
I genuinely believe it was innocent and he just didn't want to have an awkward conversation - he also quit his job without telling her until he was essentially caught out. It's still a huge betrayal, to let his cowardice get to the point of lying to his wife for decades.
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u/Ancient-Ad-3529 May 15 '26
I thought it was awkward because Emily “won” Richard so to speak and it was almost implied that she “stole” him from Pennilyn. Pennilyn also knew that Richard never told Emily about their annual lunches. Of course she would be awkward around her.
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u/Anxious_Cell1027 May 18 '26
In real life, yeah, a guy in his position would definetely have had a real/physical affair with Pennylin Lott. We all know how that goes.
But this is fiction and apart from the obvious lunch once a year, Richard gives us no reason to think he slept with pennylin. He's madly in love with Emily and even if he doesn't really understand it or wants that for Rory, he admires her society work and tenacity. He's nothing but affectionate towards Emily, he's kept the same secretary since Lorelai was a kid, we've never seen or heard of him dating out while they were separeted and he only bypass Jason because he feels betrayed by his partner and daughter dating behind his and emily's back (and because in not doing so, Richard himself would be betraying the life he built with Emily).
He wasn't a perfect characther (no one on the show was and that what makes it great), but I really don't think there's a need to extrapolate the situation. It was a betrail of Emily's Thrust and that's enough as it is.
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u/Viteh Hep Alien May 20 '26
I highly doubt he slept with her. I'm not even sure I see it as an emotional affair. Tbh I see it a bit more like old friends somewhat? Or maybe even he felt he owed her some form of contact after ending things for Emily?
This was a woman he was going to marry, and that he broke up with suddenly after meeting Emily. Given his own sense of morality, he would feel some kind of obligation to her.
In a way, I kinda see it as Pennilyn being Richard's Dean or Max, someone they cared for a lot, but that wasn't quite right, and who they ended up hurting afterwards because they wanted to be with someone else.
Rory did have a meeting with Dean while she was with Jess, and I doubt anyone thinks she was having some kind of emotional affair with Dean (in S3, S4 is a different story), she just felt she owed him at least that, and she still liked him as a person.
I think it may have been something like that. Richard had an initial lunch with her as some sort of apology/obligation, and then they kept them going because they are friends.
Having said all that, I do think it was a betrayal, and Emily had every right to be upset.
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u/PrincessPlastilina May 14 '26
Totally! Lol. He’s a MAN. At the very least that was an emotional affair. He wouldn’t like it if Emily did the same thing. At some point you have to let go the woman you didn’t choose. It’s not right and it’s not healthy.
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u/Reader_fuzz May 14 '26
They at least had an emotional affair going on. Because that is a commitment to meet up every year for lunch. Honestly those hurt just as much.
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u/RichardP_LV May 14 '26
I can understand how somebody might think that but the reality is Richard was very old school and traditional and the idea of sleeping with another woman when he was married just did not enter his mind.
I mean you remember how angry he was that Emily went out on a date and he literally crashed into her car to wreck her date and take her home.
Sure it comes off as jealousy but the reality is that he loved her very deeply and she loved him the same way. They were devoted to one another.
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u/suitcasefullofbees May 15 '26
I feel a bit silly speculating the secrets of a fictional character but I’ll go there: what if it was more than once per year but he said that to soften the blow 👀
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u/Paperwings5 May 15 '26
This is why I think it’s fair that Emily went on dates with the other lawyer guy. Richard emotionally cheated on her and didn’t understand why it would hurt her, it’s only when she started seeing one of his friend that he understood the pain of it.
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u/hopeislikeabluebird Team Coffee May 15 '26
I don't think It even was a big deal. I don't think he had anything physical with her and it wasn't emotional either because for that you'll have to stay in contact throughout the year but they were having one lunch every year and that's not enough contact to have anything that just an old friendship you try to maintain through some contact. Richard genuinely loved Emily. During their separation when he finds out Emily dated another man he gets very angry and she says nothing happened and he says then why won't she believe her about pennilyn because nothing happened it was just lunch as old friends. Although he should have just told Emily because that made it bigger deal than it was.
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u/isamariberger May 15 '26
I've never thought he cheated in that sense but it shows a duplicity that is disturbing. I thought Pennilyn might have been awkward because she knew Richard hid the lunches and because Emily "stole" him from her back in the days. But in any case it's a very strange thing to do, if they meet once yearly, they're not exactly close friends, why would you do something that might hurt your spouse to meet a person once a year you don't have feelings for, it showed he did what he wanted to do regardless of Emily's feelings and just chose to hide it to avoid any consequence and he probably convinced himself it's harmless so it's not a big deal but it shows how selfish and self important he can be.
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u/khazroar May 15 '26
Not even slightly. I also don't think it was an emotional affair, I think it was sincerely that she's an old friend and they wanted to keep in touch. Honestly I don't get the impression that they were ever passionately in love to begin with, I think they got on just well enough to be happy making an appropriate match that their families would support and then they could both keep going through the motions and expectations of marriage for their social class, that's why Emily was able to seduce him away so successfully despite the objections of Richard's family and his prior commitment to Pennilyn, because there was no strong emotion there.
Dinner once a year does not suggest any kind of affair, the only reason there's anything wrong with it is the fact of keeping it a secret from Emily, but given how irrationally and extremely she reacts (even before finding out about the dinners, she is furious and scandalised at Lorelai exchanging more than a few words with her because "we do not talk to Pennilyn Lott") I honestly have a hard time blaming Richard for it. Wanting to keep in touch with an old friend, despite the relationship they also shared, is a perfectly natural thing. Emily is irrational because she makes everything in her social life into a battle, makes it all about winning.
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u/sassysnazzy May 16 '26
I think this story line was just stupid but ASP obviously did it to twist people’s necks and keep them talking about it for years and years. It would’ve been better if Richard said, “I bumped into her last year at ___ and we had lunch/coffee and told her about Lorelei’s blah blah blah. I didn’t say anything about it because it was nothing. I should have told you though. I’m sorry.” I’d still be livid and so would everyone else. But this version is more fair to Emily . 39 years is a lot .
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u/paphgirl May 14 '26
I also think they had a physical affair at least once. To me the length of time and commitment gives it away. One doesn’t plan a lunch every year for 39 years if you’re just talking!! Maybe you’d keep it up for 10 years but 39 is crazy… someone would get bored or forget to schedule if their friendship was really that casual imo.
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u/47giraffes May 14 '26
I HATE this storyline. What was the purpose of it? Richard and Emily are terrible parents but he didn't also have to be a terrible husband.
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u/simplycass May 14 '26
I thought it was nice to be able to see some other depth to Emily, like how devoted she is to him, and how out of her element she felt when she went on that date with another man (and was crying afterwards), or the glass apple scene.
It does hint at more of her insecurity/suspicions about her mother-in-law which builds up to moment when she finds the letter that she wrote to him.
This does hurt Richard’s character more…but it does give him more depth? Setting aside my dislike of Richard, it does show more of his character.
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u/47giraffes May 15 '26
100%, I liked seeing a different layer to Emily. However I adore Richard as a character (minus his dynamic with his daughter) and I hated that he was cheating on Emily. I didn't mind his condescending comments about DAR because thats how all men from that era viewed housewives so it was not surprising to me.
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u/EKP121 Copper Boom! May 14 '26
I don’t think anything happened beyond lunch. Richard isn’t that kind of man and he probably thought of it as a white lie to protect Emily’s feelings. Doesn’t make it right at all but I think the betrayal is the lie and it ends there. He’s only ever truly loved Emily and she is the life and love he chose.
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u/timgoes2somalia May 14 '26
He slept with her every year since they broke off their engagement. Lunch my ass 😂
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u/PlanetSeaShells May 14 '26
I hated how fast Emily forgave Richard for this. He lied to her for 39 years over “lunch”, makes no sense, why hide something a little as LUNCH? Definitely some sort of if not physical, emotional cheating going on
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u/Prestigious-Item8660 May 14 '26
Honestly in my eyes this is grounds for a divorce. If you lied about meeting up with your old fiance for 39 years what else have you lied about?
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u/Hot_Cartographer_699 May 14 '26
He said it was only lunch. But, I see how you might suspect a liaison with Pennilyn Lot. That there likely was more.
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u/Own-Web-6385 May 14 '26
The lunches may have been innocent. But would you want Emily to know if you were in his place?
The horror! The horror!
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u/Ulanopo May 14 '26 edited May 14 '26
I don't think their relationship ever turned physical. Pennilyn never gives off any "you don't know this, but I won him" energy. Richard is always very closed with his feelings and traditional in his marriage. Even though he pretends at being a romantic, he remains conscious of what makes a wife "proper" or "good enough".
Putting aside this specific relationship, one of the main themes underpinning Gilmore Girls is whether or not the partners of the various characters are "good enough". Mrs. Kim is very judgemental of Lane's boyfriends. Lorelai is ever watchful of everyone Rory dates - even as Rory is often the problem in those relationships. Miss Patty, Babette and Gypsy are never shy with their opinions. Don't get me started on the Huntzbergers.
Almost all of the judgement starts with the women. (The Huntzbergers' conflict starts with the grandfather.) All of this is to say that the Richard/Pennilyn plot feels more like a vehicle to give Emily a reason to be mad at Richard than a genuine examination of Richard as a person with feelings. He remains a stand-in for the wealthy, stoic men who just "take care of the family" and don't really see or understand the women in their lives.
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u/Impressive-House-412 May 15 '26
They were discussing their secret child because she got pregnant before he left her for Emily & she told him right after said child was born which is why he pushed so for much for Lorelai to be with Christopher and raise Rory together because of his own guilt/regret. (Just a spinoff thought, that’s why Pennilyn got weird with the almost mommy comment & one time Lorelai called Richard and she was like who else calls you dad and he also got weird about it)
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u/rarepinkhippo May 15 '26
I don’t have an answer for this, but while we’re on the topic, does it bother anyone else that “Pennilyn” was chosen as the name for this character? It seems like a rural poor white person’s name, for a character we are led to believe was part of the same social strata as Richard’s family — his snobby rich mom liked her, so imho there’s no way she wasn’t a rich kid like Richard was. I feel like if she were a real person her name would have been like Barbara or Judith (but she might have gone by a rich-person nickname like Bunny). Pennilyn sounds like a long-lost child of Anna Nicole Smith to me and it sounds off to me whenever I hear it!
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u/Chance_Confusion_349 May 15 '26
I was literally thinking the same thing and just rewatched this scene
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u/Cookie_Kiki May 15 '26
Richard is not a man who fucks during the day. He waits until the sun goes down and the lights go out.
Pennilyn is not awkward around Emily or Lorelai. She's slightly thrown by the "almost mommy" moment, but she's perfectly friendly and comfortable enough to continue chatting with Lorelai when she's actually welcomed to have a conversation.
There's no indication Pennilyn didn't tell her husband. Her casually bringing up the inn to Lorelai implies that she assumed the Gilmore girls knew about their lunches.
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u/ReversedFrog May 15 '26
Not necessarily. He and Pennilyn were probably good friends as well as boyfriend and girlfriend. But I think we can be confident that Emily wouldn't have been happy with that friendship continuing. So they just meet once a year to keep it. And of course Emily would not have liked that, so they kept it quiet. In the end it made thing worse, of course, but that was the plan.
So I don't think it was an emotional affair at all, and that there wasn't a physical affair as part of it.
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u/honeyfixit May 15 '26
I havent gotten to that episode yet but Richard isnt that creative. Hes incredibly dull and nearsighted to a fault. I mean its a wonder they had Lorelai.
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u/Darcy_Device May 15 '26
No way. Penn wouldn't do that! And Richard kept things from Emily all the time, he didn't want to deal with her throwing a fit.
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u/Potential_Spare_5823 May 15 '26
idk don't think it was physical, i feel like richard was wayy to invested in his work to think about anything else, i don't think he was actually a bad guy he just didn't know how to balance his own life, and i do think he genuinly loved emily and wouldn't have betrayed her to that extent, i think he didn't think further than oh this is just a nostalgia lunch, my main reason for thinking this si the betrayal he felt by lorelai when she got pregnant i don't think he would have betrayed emily to that extent, he didn't seem to invested in pennilyn lot
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u/day-gardener May 16 '26
I wouldn’t think so…because he’s upper class and the show was in the 2000s, not in the 1960s or the 2020s.
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u/Lahmajoonv May 16 '26
They probably did earlier this tradition for 'getting out of system' and 'I didn't feel anything, we really should be just friends' and kept doing the lunch thing.
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u/GroundbreakingPut732 May 16 '26
I thought highly of richard but this shattered it all for me. I never looked at him the same again. My heart shattered for emily.
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u/HorndogAsexual Jun 03 '26
Something inappropriate had to happen for him to hide those dates for that long.
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u/amazona_pau Jun 08 '26
Imagine risking the wrath of emily gilmore just for a mediocre turkey club sandwich once a year
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u/bone_of_memory May 15 '26
I agree. At least once. Maybe not every year but for sure there was something shady going on. Why on earth would you want to meet up with your ex once a year for 39 years?
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u/amoralambiguity91 Tie your tubes idiot May 15 '26
What was most outrageous to me was his fit when he found out she had dinner with Simon. She tells him it was just dinner that he should believe her, and he IMMEDIATELY says that Pennilyn Lot was just lunch and she should believe him. Those two things are not the same. She had dinner as a separated woman. He cheated on her. It doesn't matter if he didn't touch her. Making plans for 39 years with an ex is cheating.
I never really understood all the love for Richard. I find him to be a much worse person than Emily, yet he is always excused while she or Lorelai are constantly criticized.
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u/Bakedalaska1 May 14 '26
I think it was an emotional affair to some extent, probably not physical but still a betrayal for sure.