How To Ask A Guy To Hang Out Casually Without Making It A Big Deal

We are now well into the 21st century, which means it is more than acceptable for a woman to ask out a man. And yet, a lot of people still find the prospect terrifying. Centuries of societal norms are hard to shake, but don’t be discouraged. Here is a foolproof guide for asking a guy to hang out without embarrassing yourself.

  1. Give him an easy out. You don’t want him to feel cornered. When you ask him if he wants to hang out, make it easy for him to say no. Say something like, “I’m not sure if you have plans later, but if you don’t…” That gives him a ready-made excuse in case he doesn’t he’s not interested. If he likes you, he’ll leap at the chance to go out. You’ll learn a lot by giving him a way to turn you down without looking like a jerk.
  2. Default to humor. If you’re feeling uncomfortable, telling yourself to calm down will only make it worse. Instead, embrace your nerves and make light of the situation. Humor and self-deprecation are charming. Use a terrible pickup line that makes you cringe. You can even tell him that you’re nervous and don’t have much experience asking men out. While this may sound mortifying, it will actually diffuse whatever awkwardness is hovering around you and win him over.
  3. Don’t sound like you’re asking a favor. The guy you’re asking out will likely be flattered that you’ve gone to the trouble to ask him out. You have no reason to sound apologetic. You are not inconveniencing him by asking the question. You’re not forcing him to do anything. If you make it sound like going on a date with you is a burden, he’ll have every reason to see it that way.
  4. Be specific. Saying “it would be fun to hang out sometime” saves you from direct rejection (no one is going to say “no, we shouldn’t” to something so vague) but it’s also a difficult proposition to follow up on. In a way, you’re just inviting him to ask you out. To do the asking out yourself, you’ll need to actually invite him to something. If you’re too nervous to ask him out on a one-on-one date, you can tell him you’re going out with friends and it would be fun if he joined.
  5. Do it over text if you have to. If you’re really shy and have already failed several attempts at talking to him in person, it’s perfectly okay to text. The downside of doing this is that you won’t be able to gauge his response outside of what he texts back. If you ask him in person, you’ll be able to interpret his body language and tone of voice. With a text, you’ll have to decipher his reaction from whatever he writes back.
  6. Find the right moment. Context is everything. Asking a guy out who’s married and has three kids is setting yourself up for failure because it lacks the right context. Making sure that the guy you like is single is step one, but there are a lot of factors that go into finding the right opportunity. Choose a setting where he isn’t distracted by friends or in a hurry. If you choose the wrong moment, you won’t get the answer you’re hoping for even if he is interested.
  7. Test the waters. You don’t have to jump into it completely blind. If you know him already, you’ll be able to predict how he’ll respond if you ask him out. Do you have good rapport? Do you sense an undercurrent of flirtation in your conversations? If you see him across the room on a night out, try developing a connection from a distance at first. Catch his gaze to see if he’s noticed you. If he seems interested, you have every reason to be confident when you approach him.
  8. Buy him a drink. If you seem an attractive guy and are feeling particularly bold, you can send him a drink through the bartender or ask him directly if you can buy him another one of whatever he’s having. This is a confident move that will, if nothing else, gain you his respect. Remember, there is nothing embarrassing about letting a guy know that you find him attractive. The worst-case scenario is that he’s flattered but not up for a date.
  9. Don’t overthink it. One of the easiest things to say and hardest things to do is be open to rejection. Don’t spend weeks thinking of what you’re going to say in fear that the wrong approach will be the end of the world. Don’t start imagining how devastated you’ll be if he isn’t interested. If you approach him feeling like you have everything to lose, he’ll know it. He will sense your intensity and it might make him uncomfortable or intimidated even if he really likes you.
  10. Be straightforward. Awkwardness is just a state of mind. If you’re confident and walk up to a guy you’ve been swapping glances with and ask him out, you’ll probably be successful. He’ll be so attracted to your assertiveness that he won’t think twice about his response. The more you project self-assurance, the more likely he’ll be to take you up on your invitation.

What should you do when you hang out with a guy you like?

If the guy decides he wants to hang out, then you need to decide what to do. It doesn’t have to be anything extreme and it probably shouldn’t be early on. Instead, you want to go for something super chill and relaxed that’s still a lot of fun and gives you a chance to get to know each other. Here are a few ideas for where to start.

  1. Grab some coffee. This is way more relaxed than going for drinks and is a great activity to consider for when you finally hang out with this guy. Whether you chat in a busy Starbucks or hit up an independent cafe in your area, you can’t go wrong with a bit of caffeine and conversation, right?
  2. Go bowling. Maybe you haven’t bowled in years, but chances are you remember it as being a lot of fun. Why not book a lane for a few games and let your competitive side come out? You’ll be able to grab food and drink between frames and you’ll never have to deal with any awkward silences because before you know it, it’ll be your turn.
  3. Check out a new restaurant in town. If you both consider yourself foodies (or you’re just hungry and need to eat), grabbing food from a new place that everyone is talking about or that you’ve been dying to try can be a great option for something to do when you hang out with this guy. Even if it’s not all that great in the end, you’ll at least be able to bond over the experience.
  4. Try karaoke. This is for the adventurous, of course, but it’s definitely worth considering if you’re the opposite of shy and up for something a bit different. Get your playlist ready and belt out your favorite tunes at the top of your lungs, not worrying at all about how you sound. He’ll definitely get the message that you’re confident and a lot of fun to be around.
  5. Hit up the farmer’s market. Again, totally casual thing to do. Pick up some fruit and veg and some yummy baked goods and walk around the farmer’s market on a nice day. If it’s near a park, you can then grab a bench and chat before going your own way.
  6. Catch a sports match. Whether it’s baseball, basketball, or any other sport, going to a game together is a great thing to do when you hang out with a guy you’re interested in. Chances are, he loves sports and will welcome any opportunity to hit up a match. If you’re into sports too, it won’t be boring for you either and you can get into cheering for the team together.
  7. Attend a street fair. Again, super casual and plenty of food options (noticing a theme here?). Walking around a street fair is great because you get to try so many different things and chat as you go along. You can even share some dishes, which will bring you closer together. Bonus points if there are rides – get some tickets and go on one!
  8. Go to an art museum. It might sound boring to hang out with a guy at an art museum, but it’s definitely not. It shows him you’re cultured (and lets you see if he is) while exposing you to some great works that can be thought-provoking and emotional. Plus, not all museums are about centuries-old paintings. There are museums for all kinds of things. Do your research and you’re sure to find a few that appeal to you.
  9. See one of your favorite bands in concert. Music bonds people, especially live music. If you’ve chatted about your favorite musicians in the past and they just so happen to be coming to town, why not grab tickets and go together?
Rose Nolan is a writer and editor from Austin, TX who focuses on all things female and fabulous. She has a Bachelor of Arts in Theater from the University of Surrey and a Master's Degree in Law from the University of Law. She’s been writing professional since 2015 and, in addition to her work for Bolde, she’s also written for Ranker and Mashed. She's published articles on topics ranging from travel, higher education, women's lifestyle, law, food, celebrities, and more.