I’ve been dating a guy since January, and was just going through our text messages. I noticed that most times I’m the one who sent the “when can we meet next” text, or was the one to mention it in person – but then once I do he comes up with ideas and is quick to execute them.

I’m more of a plan-ahead type person than he is, so that could be part of it. I’m just surprised to realize that is really almost always was me. He is definitely into me. It’s official, exclusive etc – although again I asked and he 1000% agreed. Every time we say bye he is like “lets meet again soon” but doesn’t nail down a date/time in the moment.

I kind of feel like I’m chasing too much! Should I not ask for the next date and see if/when he does? I end up asking because I’m trying to make plans and leaving space for him – if he asks too late and I’m busy so be it I guess. I wasn’t do that because that didn’t seem productive when trying to develop a relationship.

Bring it up – any suggested wording? I did tell him today that I need to plan ahead a little bit. Just like if on the weekend he wants to meet “after work one day” I want to know which day.

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There are a couple interactions that are like:

*Context: at some point on the weekend we had talked about meeting during the week. We usually meet on Wed/Thurs because of work*

(Tuesday evening) Me: Hey! Do you want to hang out Wednesday or Thursday?

(Tuesday evening) Him: Yeah I’d love to hang out on Wednesday, I was going to ask!

My question is . . . . when were you going to ask!?!

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TL;DR – He seems very interested in me when we are in person and once I prompt him plans out nice dates. He’s definitely a bit shy in general, but I’m concerned that I’m the one pushing the relationship along – when’s the next date? are we official? come meet my friends.

6 comments
  1. Why play games or over think it? Its obvious the guy likes spending time with you and is putting in the effort to make you happy. Honestly it sounds like you have a good dynamic going.

    You could have a little chat about it but it seems like he just waits for you to let him know when you are free. Dont stress so much and just enjoy the nice relationship you seem to have

  2. This is MIT level organization. I bet your closet looks like the ones in magazines.

    Keep in mind that you may have trouble finding your organizational equal because you appear to be on another level.

    Also, I am looking for a project manager, so….

  3. He doesn’t seem enthusiastic and will take you up on your offer just to have some female company/ convenient gf. Eventually he’ll meet the girl he’ll pursue tho

  4. Don’t overthink it. Maybe he just has his head in the clouds most of the time, plus he knows you’ll ask him to do stuff. If he’s excited and happy to see you, then it could just be that he’s more laid back about communication for whatever reason.

    What made you notice this dynamic? Are you feeling neglected or unwanted somehow? If everything else is great, and you just *happened* to notice that you always initiate things, then ask him about it. See what he says. You should be able to tell by the conversation whether he’s really into you or just meh.

    My friend and I got into a screaming match a month ago because supposedly she’s the one who *always* texts first. Not true, but I do text less. In this case, it is absolutely NOT that I don’t care or that I subconsciously don’t want to spend time with her, I just legitimately don’t feel as much of an urge to chat for the hell of it. It’s not a situation where she’d never hear from me if she didn’t text first, but she’s convinced that it is, and so we’re not speaking. *Again*. All this to say, please don’t let this become an issue of grand proportions if it’s really not.

  5. He might be similar to me in which I find it extremely important to be 100% sure the other person is interested before putting myself out there to possibly get rejected.

    That being said, I have been on one “date” (just a coffee meet up) in the past 3 months of being back on dating apps. After continually chatting for a week or so I (27M) asked her (25F, I think 25ish. I forgot) if she wanted to go out to dinner.
    Initially she said she’d like to but I found it hard to gauge whether or not she was actually interested or not. Different excuses to multiple suggestions I had made. So I left it up to her to actually suggest something (as I would have said yes to anything)
    A couple days later she informed me of her situation where she was not yet ready to start something new with someone due to some past stuff.
    Fair enough. Was super glad she was upfront about it. Now I know not to pursue anything more than a friendship with her till she says otherwise. We occasionally still talk, but have never met up again. (I do enjoy having someone new to interact with, I am looking for friends as well as a relationship)

    All that being mentioned as I feel like the guy you’re dating may find it super important to have you initiate the interest (by asking to do something), so he can reciprocate (by planning the something).
    If it is an issue where you feel he needs to initiate more, let him know. More precisely, let him know it is okay to ask you out.

    I personally have a huge amount of social anxiety which prevents me from comfortably initiating conversation with anyone, let alone a pretty lady. I am working on that, but if your guy has anything remotely similar, being clear that it is ok for him to want you, would really help.
    I am unsure if 3 months is just dating or a relationship?
    “It’s official, exclusive etc.”
    To me, if we are both aware we’re ‘exclusive’ with one another. We’re in a relationship.
    Maybe you need to have that kind of chat on your next date. It may make things clearer on both ends. It would for me at least.

    All the best!

  6. Stop overthinking it. This was a bug bear like it’s for you like it was for my ex. I literally told her I hate making plans ahead because I wing everything on the weekend, because I’m exhausted from work and meeting deadlines during the week and she was my first priority anyways. I plan big events ahead of time, but rarely, weekend to weekend.

    I was dealing with a year of lockdowns when we met, I was never a super outgoing person and regressed during the pandemic. I literally just enjoy waking up on the weekend and just going with the flow. If she needed to plan something then just tell me and I’ll be there.

    She thought I was just settling and wasn’t really interested, but it was the furthest from the truth. Her behaviour and taught pattern was the way it was, because she was attractive and always had male attention when ever she wanted.

    Ironically, you’re showing anxiety like him because something you think should be “normal”, doesn’t look normal. Truthfully, there’s no normal.

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