Ask A Guy: How To Date The Outsider At Your School

Hey Joel,

I’ve known this guy since we were little, and even though he’s typically rude with people, he’s always been extra nice with me. We text a lot, work together in class, and he’s even joked about wanting to date me. He compliments me all the time and seems very happy whenever he sees me. Although I’ve always thought of him as a friend, lately I’ve been seeing him more as possible boyfriend material. Our school is having a talent show soon, so I asked him if he wanted to go with me. He said he doesn’t. He did make it clear that it’s because he doesn’t want to go to the show, but couldn’t he have suggested we go somewhere else if he wanted to be with me? Should I take this as a rejection or is he really just not into talent shows?


It sounds like you’ve found yourself someone who enjoys being an individual and an outsider. There’s nothing at all wrong with that, but make sure you’re okay with the idea of this guy not really wanting to go on traditional dates, and maybe even showing an aversion to hanging with your friends. That’s not a for sure thing, but from the guy you describe, it’s definitely a possibility.

However, the fact that you say he’s typically rude to other people is a bit concerning. Whether it’s because he is insecure or he’s genuinely a rude person, do you really want to be so closely associated with that sort of behavior? If he acts that way around and towards your friends, defending him as “that’s just who he is” may end up costing you those friendships. Think twice before you jump in.

With all that in mind, his not wanting to go to the school talent show is completely understandable. Given the personality you’ve described, an event like this is miles from his comfort zone, but it doesn’t mean he’s not into you. Sure, he could have suggested other ideas, but you could have done the same. If you really want to know if he’s into you, suggest another date that you think is more up his alley, and that will be a better sign.

I really do think you need to consider whether or not he’s solid boyfriend material. While you two may get along great one on one, the reality is that you’ll spend time with other people as a couple. If he can’t hang out with your friends, it will end up isolating you and possibly ruining other friendships you already have. Consider the larger implications of this guy before you jump in, and if you think he’s worth it, ask him out again.

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!

Ask A Guy: How To Deal If Your Boyfriend Is Pressuring You To Have Sex

Follow Gurl, Pretty Please!

FacebookTwitterTumblrPinterest, and Instagram

Posted in: Ask A Guy, Love Advice
Tags: , ,