I’ve been talking to this guy for almost two months now off of a dating app and have met up with him four times so far. We both go to the same college. On the first date/hangout or whatever we met up for a little coffee date and that was just the two of us. I enjoyed talking to him and it seemed like he did too. A week later, I was the one to ask him out. We watched a movie together so it was honestly not that good of a date, since we weren’t able to talk much. This was also alone but nothing really happened. Then he asked for the third one, HOWEVER, he said it was with his friends. It was still fun but I was pretty disappointed because we didn’t even get to talk that much?? And then for the fourth, I asked him out to go bowling. Big mistake. I chose the bowling alley that was connected to our school so after bowling, we were crashed by his friends. I was pretty annoyed by that, yet at the same time, I actually do enjoy their company. It’s just that because of it, I can’t seem to talk to him as much or make a move. Because bruh, how is it that we haven’t even held hands by now?

So my question is, is there a reason why he keeps bringing his friends along? One time he did text me how he was nervous to talk to me and complimented me, but I don’t know anymore. It just seems so counterproductive and almost disrespectful to me?

My next question is, should I still just ask him out for the next one and continue to try and pursue him? Despite the fact that I did ask him out last time? Is this even worth it anymore? Maybe it’s my pride getting in the way but it’s slowly tiring me out that I seem to be putting more effort here. Or I could be overthinking.

And if I do go on this date, I really want to try and hold his hand. But I feel like we’re both so mf awkward sometimes. I’m not sure how to go about this.

2 comments
  1. He’s either not as into you as you are to him, or he’s just nervous. With friends around, he doesn’t need to feel awkward or nervous.

    You need to have a conversation with him about this. Be blunt. Tell him you want to spend time alone with him and get to know him better.

  2. As far as we know it was only intentional once. The 4th date he probably told his friends about the date and they decided to swing by because why not, it’s right there as you said.

    If you want something alone, you go ahead and plan it and let him know your intentions. There’s nothing “embarrassing”/“desperate” about you showing initiative. He’s probably shy, so if you think he’s worth the effort then make it happen yourself.

    My girlfriend had to be the one to break the kiss barrier on our third date because I could barely muster up a big hug and I think she realized I was very slow lol.

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