Ask A Guy: How To Know If You Should Actually Make The First Move

Hey Joel,

A while ago, I asked this guy on a date (because he said he liked girls who make the first move). He said yes, and we went to a party together but nothing much happened. The worst part is that there was another girl there and he kept bringing her over to talk with us, like he liked her. Now, it’s been about a month since the party, and nothing has happened between me and the guy, but nothing has happened with him and the other girl either. Do I keep messaging him? Should I bring it up again? Should I ask when/what he wants to do?


Much like you probably talk to lots of guys that you’re in no way interested in dating, the same works with guys talking to girls. There could be one of dozens of reasons why he wanted to talk to her that night, and even if he did like her, that should in no way prevent you from going after what you want.

First and foremost, if he wasn’t keen on getting to know you, he would not have said yes to going to a party with you. That in many ways is all you really need to know. You asked him out, and he stepped through the door to see if there was something between the two of you. The fact that you’ve let things sort of dim down over the last month wasn’t the best possible move, but all is not lost. 

You’ve already done the tough part and asked him out once before, so if you’re still attracted to him, what’s the harm in asking him out again? The worst thing that happens is that he says no, and then at least you’ll know what’s what. The longer you wait, the more it will bother you and the more time he has to find some other girl that’s in no way as great as you are.

Furthermore, don’t assume that just because he spends time talking to someone else that he has no interest in you. He could have been playing a bit hard to get, or there may have been something in that moment that changed things a bit. If you really want to get to know him, ask him out again and make it something more one-on-one so you two can really get to know one another.

So get back in the ring and ask him out on another date. Plan something that you can enjoy together, and let him know that you’re interested in being more than friends. Good luck!

Best wishes,


Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

Are you confused about a guy? Do you find yourself wondering, “What is he thinking?” Tell us everything in the comments! And if you have a question for Joel, email him at!

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