I [27M] went through a breakup in April. I’ve been working on some things to try to improve myself, such as new clothes and a new haircut which I primarily did for dating apps, but they haven’t been working out much since I signed up in August.
I also signed up for a 20’s/30’s social group on meetup.com. I’ve been to maybe 15 events over the last month and a half, and about a month ago I met a girl [25F], call her Jenna, at one of these events. She was really cool and I enjoyed talking to her and getting to know her, and she seemed to enjoy talking to me too. I hoped to see her again soon.
I saw her again today at an event for the first time since, and we chatted some more about a whole bunch of stuff and she was asking me questions about myself when I asked her about herself, which felt really nice. I also know that she is single due to overhearing her taking about frustration with dating apps during a conversation with another girl (call her Tiffany).
At all of these events, including today, I’ve talked to other people too and have made some decent acquaintances (mostly male, some female), but nobody caught my interest like her, and she has seemed receptive. I really wanted to ask her out today, but I didn’t get the chance to talk to her one on one. So I did the next best thing I could — myself, her, and Tiffany were sitting next to each other on the train ride home, and I asked both of them to exchange numbers, which we all did. So, I have Jenna’s number now. We also exchanged facebooks.
I planned to text her the following sometime over the next 24 hours:
“Hi Jenna! I had a really nice time with you at the [first event] and yesterday in [2nd event]. I think you seem like a really great and cool person and I’d love to get to know you better and take you out for a drink this week, if you’re interested. Something like [popular bar near us] this Thursday or this weekend, if that works for you. Feel free to suggest something else if you’d prefer.
If not, no worries and no hard feelings, I’ll see you around”.
I realize I sound like a middle schooler here, but given that my last breakup was my first relationship and I haven’t legitimately asked a girl I met in person on a date since I was in high school, I kinda just want to get some feedback on this plan — I plan to discuss it with my therapist and my best friend as well. I could wait until seeing her in person again, but I don’t know when that will be (she’s not signed up for any upcoming events) and to wait indefinitely would be akin to torturing myself. I honestly think there’s a >50% change she says yes, but that’s not 100, and I do really want to manage my expectations the best I can, and I do worry that a “no” would really, really hurt me. So, just some words of encouragement or suggestions on how to handle things any differently than I currently plan to would be appreciated.
Thanks.
5 comments
Sounds fine if a bit more than you need. Shoot your shot. Worse thing that happens is you still aren’t going on a date with Jenna.
Hope this works out. If it doesn’t you should work on your fear of rejection. It’ll hold you back in the dating scene.
I think your plan is pretty much fine. Assuming the number exchange was natural, which it sounds like it was, I don’t see anything wrong with asking her if she wants to get together. What I would suggest is tightening up the text a fair amount. Something more like:
>Hi Jenna! I’ve really enjoyed getting to know you a little at [the events] and I was wondering if you’d like to get together just the two of us sometime? Maybe [suggest a day]?
The reason I suggest this is that the current wording is just a little bit too long, and includes too many options – it also comes off a bit too much like you’re trying to control/direct the situation. E.g. “Feel free to suggest…” implies that it’s up to you whether she can make a suggestion or not.
See if she’s open to the idea first, then you can work out the details.
Alternatively, text her about something else entirely first, see how she reacts, try to continue building rapport, THEN ask if she’s interested in something more like a date. If she’s not interested, you might be able to dodge a rejection bullet, and if she is, you’ll have some basis to build on when you’re in that often-awkward first few dates period.
>If not, no worries and no hard feelings, I’ll see you around”.
Delete that part.
I think a phone call would be better than a text, because it shows you have guts, lol. That’s a good thing. Also, you’ll get your answer immediately. With a text, you might have to wait hours. Worst of all, you might never get a reply at all.
Mmno. You’re overthinking this entirely.
Good for you wanting to ask her out on a proper date, but that’s kind of strong.
Try just texting her like you would your friend who you’d go grab lunch with. Same wording, same time frames, just normal. She’ll go.
You’re allowed to be self aware as long as you’re confident. While out you can just say “thanks for coming, I really enjoy our conversations”. Then while out ask about a place nearby and if she’s tried it…it should be natural. No need to take OLD stuff into the real world and vice versa.