AITA- how do I 30F reach out after plans fell through a few times after an awkward date with 28M?

Below are some options for how I can handle this. So, I began dating someone in December. He was quite romantic in-person, but we couldn’t see each other for a month as he was abroad and then after our second date we both were traveling a lot and dates kept not aligning but we both kept trying and we continued the connection.

When he tried to schedule our 3rd date, it was a bar near his house late at night, so i was a bit flakey however he got in touch and after i expressed not being down for late night bar dates and wasn’t available that weekend anyway he rescheduled for following week and arranged instead a very thoughtful event planned ahead and altered his travels to see me when I was in town! however he said relationship was low priority but he liked me a lot, and wanted a strong emotional connection and fun. The next few dates got kind of awkward as I didn’t allow him escalate intimacy as much as he wanted in those moments and he said it was going slow so there was some tension between us, making me feel a little uncertain and made me hesitant so i was late twice which annoyed him but he still said he wanted to go on dates with me and asked me to let him know about Sleepovers.

After our last meet, he reached out 5 days later and asked me out on another date but I was traveling and asked about Saturday sleepovers (I go to school 3 hours away, but I’m from/go to his city often) this weekend or next. He said he is availbale any day except for that saturday at 6pm, and the following Sat would be traveling but i could sleep over sunday. I said I’d let him know asap but told him sunday i couldnt make it and lets chat about travel plans. No response.

I wrote that friday to ask about his travel plans and he said he was around but had a concert with a friend at 9pm sat so couldn’t crash but is free any day. I asked about the following Sat for crashing and said it would be a lot easier for me, and he said hed have to let me know. He asked about Sunday, I said id have to let him know. He said K c ya and hung up. No pleasantries during the call/no chatting. I wrote next day (sunday afternoon) saying I woke up sick and to please do following sat without need to crash or whenever he’s in town but that i loved hearing his voice. No response. Now its almost a week.

I would have made more efforts but I felt slightly conflicted about all this effort for someone who didn’t call me until after our last date until 4 days after for the next date (altho it was for a place i mentioned wanting to go, which is sweet). It made me feel insecure slash like he was punishing me for not having sex.

He’s very smooth/eligible busy guy so I feel like he found someone else it would be easier with and he could go faster with and who is always willing to go to his neighborhood (he wants to go where wed have access to an apartment/privacy as he “isn’t in middle school” so everythings near him). but i still care a lot and feel bad baout how it ended.

1. Call and ask if he’s around for something quick this weekend (this weekend would be hard though since I couldn’t leave until Saturday to the city rather than Friday, and I have exams next week.
2. I will def be in the city the folliwing weekend, so wait and don’t reach out until next week and ask to meet then and let him cool down for another week.
3. Call now and ask about next weekend
4. Send him a playlist of songs
5. Send apology/ Call and explain that the issues were that I was out of town but that I will be in town more in May and June and July and hope we can reconnect then. Issue is he thinks i say “Sorry” too much and finds it annoying.
6. Send a fun message such as “so will i get to kiss your lips soon or not”

20 comments
  1. My honest opinion, take it for what it’s worth. Not trying to be mean here so sorry if it comes off this way.

    You are 30 years old. You can do whatever you want, date anyone you want, have the relationships you want. If you are interested in this guy you need to prioritize him – full stop. If he asks you out you need to make an effort to make it work. Don’t wait days to respond. Don’t get all flakey. Don’t say maybe maybe maybe and reschedule for whatever reason. Give him a yes or a no and go through with it.

    You can do whatever you want. You can move at whatever pace you want. But you need to put effort and energy into getting that. You need to tell this guy ‘Yes I like you but I want to take things slow’. Does that work for him? Maybe not. Maybe he’ll leave. But if that’s the case then he wasn’t the guy for you anyway.

    It sounds to me like you are trying to have it both ways – you like him and want to see him but you also are constantly giving mixed signals, either because you don’t really like him or are trying to soften the blow for it/when he leaves. That will get you nothing but unhappiness.

    Figure out what it is you want and then go get it.

  2. I would block his number. He doesn’t value you, sex is easy to find without jumping through hoops, and he isn’t offering you anything else.

  3. No offense, If be struggling if I were this guy. I don’t casually date and I want something serious, my dating actions reflect that. Relationships are work and time and when dating I show that I can do that by funneling that energy into my dating life.

    If you wanna make this work I’d recommend what would work for me. Call him and start by taking accountability without explaining unless asked. Just say, “Hey, I wanted to call and say I liked our dates but I fumbled how I handled all our dates. I’d like to start over and show you how I feel about you in my actions, I don’t think I did that very well.”

    That sounds like someone I’d want to be in a relationship with and I’d try that. I’ll even say I’ve been with women who had rough starts in similar ways but they all were straightforward in a similar way at some point.

  4. All i understood is he cant see you Saturday and you cant sunday. An annoying mouse and cat going on here.

    Let me know let you know…etc this leads to nowhere. He is fast you are slow etc…not to say all of them are, but based on my experience,a woman who insists on taking it slow and too slow is a big red flag, I’d jump ship right away.

    If you like him, let him know straight no need to zig zag around it wasting your time. At least you would know if its time to move on or not.

    Dont forget, you are 30yo, make yourself clear about your priorities and what you want.

    Good luck

  5. You have been flakey 3 times and this hasn’t escalated physically. I would say it’s time to commit to really seeing where this goes or move on.

  6. Too much effort for just casual. I’d let him go and you both can find people with more compatible schedules, locations, and desires.

  7. He’s been nicer than I would have been. If someone is “flakey” than I say bye. If you want to go, go. If you don’t want to go say you don’t want to go. I’m completely fine either way. That inbetween stuff I just don’t have time for.

  8. you first went out in December.
    it’s April….

    You’re both near 30.

    Even the most desperate and enthusiastic men aren’t going to wait 6 months at this age. it’s not middle school anymore. you also keep mixing signals.

    lastly. do you genuinely believe any man is going half a year without sex? yes he’s absolutely been fucking other girls, I hate to break it to you. Most men would be at this juncture and you’re not exclusive nor even commital….

    we don’t live forever.

    if you want a relationship, you have to decide that. right now, it seems you don’t know what you want.

    all you’re entitled to is yourself, noonne else. when you’re ready to give, be vulnerable, and open up, you’ll be ready to date vs waste peoples time

    i genuinely hope this helps give some clarity and perspective. good luck!

  9. Your post history seems to have a lot of similar posts, but after earlier dates with this guy. Repeating negative patterns – either from you or from him – are a bad sign. Sounds like you weren’t feeling secure enough to really lean into this relationship and he’s given it several chances, expressed what he’s looking for (which isn’t compatible with what you’re comfortable with) and he’s now over it.

    Although you haven’t included it in your numbered options, you did in your post title and I agree: let it die.

    Especially since you’ve gone from insisting on taking it slow to him and now responding to other comments like ‘omg I should’ve just had sex sooner’. *No, that’s not what you should take away from this situation.* The takeaway is that you weren’t looking for the same/at the same level of comfort with progressing things between you. Definitely let it die.

    Keep looking and hopefully you’ll find someone you’re more compatible with and a level/speed of intimacy you both find comfortable.

  10. With all due respect, this seems flakier than a bowl of breakfast cereal. Here’s my honest take on it.

    You left out **Option #7** in that list which is to “***move along, learn lessons from the experience and take those into how you think about a next relationship***”. Or better yet, figure out what it is that you’re *really* looking for before venturing out again. If that sounds blunt, well maybe it is, but everything I read indicates that you’re sending such mixed signals that he’s as much as given up and is likely looking for someone who is clearly focused on the same sort of relationship (or situationship) that he might be seeking.

    The way you describe him is that he ‘ticks the boxes’ of what you’d like to find in a guy. But the signals you’re giving him are either turning him off, or they’re a reflection of how you actually feel about him. If you and he felt strongly about each other, you’d make him a priority rather than a convenient option between binge-watching and sorting pillowcases. I’m willing to venture that he’s not the guy or you’d have stronger feelings. Now you’re left with fear-of-missing-out, but here’s the punchline: You already have. At least with him.

    So he brushed you off, ghosted you, what more indication are you seeking that he’s lost interest? That train has left the station, and perhaps so should you.

  11. OP has posted this same exact question on so many other subs. The advice given is the same in all the subs, she obviously is fishing for advice that suits her. She doesn’t want help, she is just looking for validation.

  12. You were late multiple times without notice and you canceled day of more than once, for several consecutive weekends in a row. He wants to move forward physically and you pushed back on that multiple times. Have you even kissed yet, 3 months in?

    People often tell women “if he wanted to, he would”. I’d be telling this dude “if she wanted to, she would”. Sure seems like you don’t.

    Let this guy go since you clearly aren’t actually interested (regardless of what you tell yourself), figure out what you actually want, then get back in the dating pool.

  13. This was exhausting to read. Feel like you both should leave each other alone at this point.

  14. Smooth guy is looking to play you. You want a relationship. He and you are not compatible.

    You mentioned not being intimate after many dates. If this is due to being traditional, you should look for ways to connect with others who share your values rather than dating apps (e.g. church, cultural connections, etc.).

    Good luck.

  15. I’m not sure you need to be that subtle here – a playlist of songs isn’t likely to achieve very much (my best guess) .. maybe this guy is already off and moving in another direction, and as you may be intuiting, things are not what they might have been before?

    Perhaps the two of you are simply not that easily ‘on schedule’, and this could have been the reason for things not easily happening/progressing before – and this is not something that you’re going to be able to easily ‘fix’? (and this is something you might need to consider & prepare yourself for)

    Otherwise, all things considered, if you’re going to try giving it a go – option number 6 sounds best to me; you’re not going to catch him at an inopportune moment by leaving him a text, and you’re being very direct and enticing.

    Good luck!

  16. Honestly, way to much thought in this, which means your not ready to be in a relationship, if I read it right he stated something to the fact of having “fun”, and yet it seems you agreed, and haven’t aloud for that fun to happen. From what I see is this guy is trying to bed you, and you’re acting oblivious to these attempts. He’s looking for his win, no matter where he can get it, hence being unavailable Saturday nights, but seems that his other isn’t around on Sunday nights. So now that your up to speed on that, it’s up to you. More then likely he’ll sleep with you and move on, cause it’s about finally getting to that point, so he can end it.

  17. Because this is too much effort for someone who’s looking for casual, and too flakey for someone who’s looking for something more committal you’re cutting yourself at the knees for it to blossom into anything.

    Figure out what you want – this feels like he’s told you he wants to not get into a relationship yet you’re making him jump through hoops as if to prove to yourself you’re worthy of more. Maybe you are, maybe not, but this approach will put anyone off

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