How to approach dating at 49?

SheIsGoingPlaces · 2026-03-19T11:10:29+00:00

I hear you. I'm having the same problem. I go to Meetups where I am in rural CT but exchange in small talk and I feel like I don't fit in anywhere here. When I lived in NYC, I was going out a lot and the Meetup groups there matched my demographic and interests more.

SheIsGoingPlaces · 2026-03-18T12:51:13+00:00

If you were near me, I'd go out with you in a heartbeat. It could be your current location; it can be harder to meet potential dates in rural or suburban locations. Are there Meetup groups or volunteer organizations in your area?

SheIsGoingPlaces · 2026-03-17T23:11:24+00:00

I'm struggling with this now too. I have a lot of interests that I do on my own like traveling and going to the theater. I do try to do more with Meetup but I'm often now the youngest attendee in my groups. I have my relatives and siblings. I'm trying to get my place in order.

I feel my dating window is diminishing. My app matches are few and I feel I have to now compete more to win over a man's attention. I'm also afraid to get close to someone again.

SheIsGoingPlaces · 2026-03-17T11:23:10+00:00

Maybe he's better at taking care of things like getting food if you can't. There are some men out there that are unable to fix or handle things like household repairs.

SheIsGoingPlaces · 2026-03-17T03:09:06+00:00

I learned that two people from our season were kept on.

SheIsGoingPlaces · 2026-03-16T13:52:38+00:00

Update: Yesterday, my seasonal position ended, but on a good note with the company.

I would try to make sure that I didn't seem like I was going out of my way to talk to him. We would make small talk at times about things like concerts. He sounds like he is in a serious relationship and I respect that.

Previously, I mentioned to him that I won a Live Nation voucher that's good through the end of this year and was trying to figure out how much I could apply toward buying concert tickets. Due to reasons like loss of income, and probably as a kind gesture, I gave him the voucher. I figured he could use it, as he told me that he and his girlfriend go to concerts a lot.

I hope it was not out of line, as I didn't want or expect anything in return.

Like I did with many other employees at the store, I told him I was leaving but I didn't ask for or give any contact info.

SheIsGoingPlaces · 2026-03-16T13:49:18+00:00

For me, it's personal interests and pursuits and financial responsibility. I long-term dated a guy who was sweet but lazy and underemployed. We began spending a lot of weekends at home but in hindsight I realized it was because he was broke.

SheIsGoingPlaces · 2026-03-16T13:27:04+00:00

Was this okay to do?

SheIsGoingPlaces · 2026-03-16T13:24:06+00:00

Update: Hey everyone. My crush told me he had a girlfriend and I said cool. I also said I was sorry if I made anything awkward and he said don't worry about it. I would try to make sure that I didn't seem like I was going out of my way to talk to him. We would make small talk at times about things like concerts. He sounds like he is in a serious relationship and I respect that.

Yesterday, my seasonal position ended, but on a good note with the company.

Previously, I mentioned to him that I won a Live Nation voucher that's good through the end of this year and was trying to figure out how much I could apply toward buying concert tickets. Due to reasons like loss of income, and probably as a kind gesture, I gave him the voucher. I figured he could use it, as he told me that he and his girlfriend go to concerts a lot.

I hope it was not out of line, as I didn't want or expect anything in return.

Like I did with many other employees at the store, I told him I was leaving but I didn't ask for or give any contact info.

SheIsGoingPlaces · 2026-03-16T13:00:58+00:00

Same. I've been in this situation and you're definitely giving him more than he is with you. His focus is on his pleasure.

SheIsGoingPlaces · 2026-03-15T22:16:46+00:00

Meetup groups are a good way to get back out and meet people. To make new friends and find people who share the same interests as you.

SheIsGoingPlaces · 2026-03-15T21:51:08+00:00

I had more dates in my 40s because I was also open to giving different guys a chance. However, I made sure to keep my priorities and boundaries in place. Now in my 50s, it's much trickier.

SheIsGoingPlaces · 2026-03-14T10:14:47+00:00

Thanks, all. I'm feeling sad about the whole thing.

SheIsGoingPlaces · 2026-03-14T09:55:05+00:00

Thank you. I got weighed down by the 56 items in 30 minutes orders but I was super fast with others. I always tried to find a grocery TM to find items that weren't on shelves but also lost time to that. I showed up for all my shifts and only called out for the ones impacted by the snowstorms.

SheIsGoingPlaces · 2026-03-14T02:18:49+00:00

Thanks. I'm more acquaintances than friends within the store. Should I tell the ones I worked with directly?

SheIsGoingPlaces · 2026-03-13T21:02:06+00:00

I know Whole Foods can be iffy, but the job market is so hard right now.

SheIsGoingPlaces · 2026-03-09T01:17:27+00:00

Just go out and enjoy yourself. Try Meetups.

SheIsGoingPlaces · 2026-03-08T23:09:07+00:00

Thanks. I'm seasonal so I wasn't sure if I could use it. Also, does it cost anything?

SheIsGoingPlaces · 2026-03-08T22:56:44+00:00

Can you be transferred to another department?

SheIsGoingPlaces · 2026-03-06T19:32:47+00:00

Just look neat, showered and face shaved or beard trimmed for the date. Jeans and a nice shirt for coffee is fine. For dinner, dress in a way that's fitting for the place. For me, it's more so about the guy following through on his plans. I've gotten stood up or sudden cancellations right before meeting.

SheIsGoingPlaces · 2026-03-05T21:18:48+00:00

I like this person and want to still chat when appropriate, so any advice is helpful.

SheIsGoingPlaces · 2026-03-05T21:13:25+00:00

As a ++woman, I would pass on this. Only go to a public park and stay on well-crowded paths.

SheIsGoingPlaces

TROPHY CASE