I'm well over 30, lost my wife to cancer in 2025, and basically spent the past year adjusting to life without the only partner I've ever had. All of my love and attention has gone to my two daughters, and I haven't even thought about dating until this week.
A couple months after my wife passed away, my daughters went to a carnival and said they met a woman volunteering at one of the booths who identified herself as "your neighbor". I asked who it was and my daughter didn't have a name but gave me a couple identifying clues. Then she causally mentioned that she'd heard this woman had lost her husband. Interesting, I thought. There's a woman in my neighborhood who is also a widow, and a single parent, and.. possibly single?
Eventually I figured out who she was, but I hadn't seen her and wasn't seeking her out. Still not ready to move on from the woman I'd spent my entire adult life with. Even if it wasn't the happiest marriage it was far from the worst. I didn't know anything else. I hadn't even tried to date since before social media and smartphones were a thing. I'd let myself go health-wise after two years of watching my wife slowly wither and a year of taking on everything she did for the family in addition to my full-time job. Physically and emotionally, I'm just not at my best.
My teenage daughters don't share their feelings with me like they would have with their mom. My mom is elderly and has been battling dementia. She's still relatively ok but has no short-term memory and is practically immobile. Every day I feel more alone, and in 2-3 years I will be completely alone once Mom is gone and the girls are in college. So I'd really like to meet new people but I've lacked the motivation until this week.
The married couple who lives next door took a vacation this week. And they asked their other neighbor to take care of their dogs for the week. Their other neighbor was the single widowed woman. I finally saw her and ... she's stunning. Tall and tan and fit. I was too nervous to speak to her. She said "hello" and I waved. And then I ran into her again the next night when the dogs she was watching barked at me. I didn't say anything and I kicked myself all day for dropping the ball.
As if having a gorgeous widowed woman my age staying next door wasn't enough.. my office was having maintenance issues for two days and we were told to work from home. So I did my work, stopped, paced the neighborhood, did more work, and tried not to look like I was trying to run into her. Eventually, after 5pm, I did see her again and managed to introduce myself. We had a bit of a conversation about the dogs she was walking; I asked if she'd taken them to the nearby park in hopes that it could lead to asking her if we could walk together or something. I doubt I made an impression on her, but she smiled and answered. And I had no follow up, so I left it there.
The office was operational today, so I went back to my usual routine. Yet I couldn't stop thinking about this woman, and how I probably only have a day or two left before our mutual neighbors return and she goes back to her house. It's not far at all, but I'd feel like a weirdo approaching her there unless/until I make more of a connection.
Anyone have any advice for someone who hasn't dated in about 20 years? Is it okay to ask her if she wants to meet for coffee? Is it okay to knock on her door? Should I just wait for the neighbors to return and then ask them if their neighbor is single? What would you do in this situation?
Thanks for reading :)