Am I Waiting for Something that’s Not Going to Happen?

Dear Guys,

I met this guy on a dating app. We talked for about two months and went out a couple times for beers and to a baseball game. At the time he was in duty in another state for the military so we only saw each other on weekends when he would come home. I told him I liked him and he said he liked me too but the timing was really unfortunate because of his military status—he never knows what is coming or where they will send him next, but that once he moves back we can see then how we feel.

I did start dating someone for a couple of months but it just wasn’t what I wanted so I ended it. Literally the day after I ended things he texted me asking how I was. He knows that I dated someone and knows why I ended it. He asked about it a lot and I feel like he was looking to find out what I don’t like.

But now we’ve hung out the last three weekends in a row and I just can’t get a read on him. I still have those same giddy feelings about him and am super attracted to him. But I don’t know how to go about asking him. I don’t want to push or put pressure on him to tell me how he feels. Part of me really thinks he likes me and is just taking things slow but then part of me feels like he just thinks we are friends and is comfortable around me.

We’ve only hugged once and that was the first time we hung out I made him get out of the car when he dropped me off. Now he just leaves. No hug. No nothing. He responds to all of my texts. He pays for all of our dates even when I ask him and put my card out. He remembers everything I tell him. Playfully teases me and jokes around. But I know that he’s active on the dating app still so I don’t know what to think. What are some things I can say to find out that won’t make him feel like I’m pushing things between us. I really don’t want to seem obsessive. I just really like him and cannot read him whatsoever.

Thank you


Dear Justine,

We understand why you might be confused. Let’s try to figure this out together.

A few questions:

  1. Who initiates your dates? Does he ask you or do you ask him?
  2. Does he initiate any communication between dates or is it just him responding to your texts?
  3. Do you know if he’s dating other women? (You said he was on the app so we weren’t sure.)
  4. Does he ever touch you affectionately just to touch you? Like his hand on your hand, or his hand on your shoulder or back?

The fact that he keeps asking you out—we’re assuming—pays for your dates and seems interested in learning about you are all good signs. But typically when a guy is interested in a woman, he’ll try to show her by finding ways he can be affectionate to her, like touch her, like we mentioned above, but also communicating with her a lot and maybe even bringing small gifts. And most guys by the third date might have tried to at least kiss you.

So here are three possible explanations as to why he might not be doing these things.

  1. He’s either not interested or sees you as a friend.
  2. He’s very shy.
  3. He can’t get a read on you so he’s not sure if you’d welcome any advances of his. Maybe he thinks you’re out of his league.

So what can you do to figure this out?

At this point, it seems there’s not much to lose. Obviously you like him as more than a friend so if nothing changes eventually you’re going to get frustrated. So maybe you need to show him that you’re more interested rather than ask him? (Obviously, you need to feel comfortable doing this.) How do you do that? Well, maybe you get a little more touchy with him. Like find ways to touch his hand, or arm, while you’re talking. Or if there’s an opportunity, try to snuggle up to him, like when you’re out at a bar or whatever. You could also plan a date yourself and ask him out. Like get tickets to a show he might like, or a game, or a comedy act. And prepay so there’s no weirdness about it. Or cook dinner for him at your place.

If you don’t want to do any of those things, then you’re probably going to have to actually tell him that you’re interested. You don’t have to come right out and tell him, but you can compliment him and say that you think he’s a very cool person, and tell him that he’s different than other men you’ve met. If he can’t read between the lines, then you’re going to have to tell him directly. But we’d recommend giving this a few more dates just to see.

If none of this works, or he declines your date invitation then you should have a pretty good idea he’s not interested. But we hope that doesn’t happen and that he eventually shows you he’s interested.

Thoughts? Questions? (Leave below in the comments section.)


ps. We also recommend our book for you to read. “Inside the Guy’s Mind.” You can find it on Amazon. It might give you some much needed info on guys in general. (And please let your friends know about us. Thanks.)

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