Before You Take A Chance On Him, Ask Yourself These Questions

Ever have that feeling when you meet a guy where your heart says yes but your brain says no? It’s really difficult to know which part of your body you should listen to. Oftentimes, your brain tries to steer you away from bad news guys, but in your heart, you know that everyone is worthy of a chance. Here are a few things to consider before asking him out.

  1. How did his last relationship end up? You might not know, but if you get close enough with a guy, surely an acquaintance or two (or even Google, if we’re being honest) might clue you in. If he has a restraining order against him that’s relatively recent, that’s a plenty good reason to back away. Sure, it could have been some kind of disagreement, but it’s a huge red flag that he doesn’t know how to respectfully treat women.
  2. Does he have a lot of friends? People are much like the friends they keep. If he has a lot of friends who are total jerks, he may be the same. Guys who have one or two close friends could be loners. If this guy approaches you awkwardly and fits the “loner” category, it just means he might not be as well-versed in social interactions as a guy with a huge group. Give him a chance because he might end up surprising you.
  3. What do your friends think? Speaking of friends, their input can have a lot of value. Maybe they’ve heard stories about this guy that haven’t made their way to you just yet. Ask them what their first impression is. If it’s a resounding “no way,” you should listen, especially if you’re on the fence. Your friends may not be right, but they’ll at least be able to offer some different perspectives.
  4. Are you even ready for a relationship? If he’s a guy who likes you and has tried multiple times to ask you out, you may be wondering whether or not it makes sense to take a chance on him. But the first question you need to ask is, do you even want a relationship to begin with? Maybe it’s not the guy that’s questionable. Maybe it’s the timing.
  5. Does he seem genuine? If he’s been trying to impress you for weeks, you may wonder if the grand gestures might end the second you say “yes.” Now, of course, you should expect them to drop a bit—now that you’ve agreed to date, he got the chance he was looking for and being “on” all the time is exhausting for anyone—but if his entire personality changes and it seems like he’s a completely different guy than he was in the courting stages, that’s a bad sign.
  6. Is he too much? Speaking of courtship, some guys can overdo it. Getting flowers and gifts is nice, but daily reminders that he’s into you might send a completely different message. There’s nothing that scares a girl off more than a guy that seems too clingy and attached before the first date even happens.
  7. Does he have a history with anyone you know? The best guys have no attachment to anyone else in your group. It’s possible (and likely) for mixed friend groups to include some hookups, but when that happens, there are often emotions attached. If your best friend is into this guy and you’re just not all that sure, it might not be worth the risk. And if this guy is decent, he should understand that.
  8. If he’s online, does his profile sound too intimidating? Online dating is one of the top ways people meet each other these days, which means it’s fair to be a little choosy. If his interests sound a little scary or his personality is a bit too intense, this guy probably won’t make it up to you in person. Ask questions if there’s anything on there that makes you worried, and see what his response is. Don’t be afraid to call him out. Your head will lead you in the right direction from there.
  9. Are you attracted to his personality? Of course, it’s important to be attracted to his photos, but it’s much more important to be attracted to his personality. That’s the section of his online profile that he might not fudge. Photos, on the other hand, may be a little old or just taken from one specific angle. Looks change over time, but a good sense of humor and honest responses about personal strengths and weaknesses can go a long way.
  10. Do you both want the same thing? If you both want a hookup, that’s easy. But if you’re looking for a long-term relationship and he’s looking for a summer fling, it may not be worth it whatsoever. It’s important to be upfront right off the bat. You both may very well change your minds, but banking on that is a gamble.
  11. Are you just lonely? If a guy has been actively pursuing you and you’re on the fence, it may be your loneliness telling you to say yes. If you haven’t been in a relationship in a long time, it makes sense to jump on something that’s offered up, even if you’re not really feeling it. It’s nice to give this guy a chance, but it’s also really unfair to him if you’re with him just based on boredom or just to help raise your confidence. Ask him out for a friendly cup of coffee and see if there’s more legitimate chemistry there than you think, but don’t lead him on if there isn’t. He deserves more.
Karen Belz is a New Jersey native who is currently living in Maryland. She has a Bachelor’s Degree in Speech Communication with a focus in Broadcasting and Print Media Studies from Millersville University of Pennsylvania. Since graduating, she has written for sites like LittleThings, HelloGiggles, and Scary Mommy and is currently an e-commerce editor at Bustle.

When she's not writing, she enjoys making her phone run out of memory after taking too many photos of her dog. You can find her on Twitter @karenebelz or on Instagram @karenbelz.