How to Ask a Guy to Hang Out Through Texting

Boost his ego a bit to get things started.

Tell him he’s charming, funny, or smart before you ask. Butter him up with a few messages that talk about some of his qualities that you like and admire. He’ll love it and he may be more open and receptive to hanging out with you when you ask him Try texting, “You might be one of the funniest people I know” or “You little charmer you.” You could also try, “It’s always refreshing to talk to an intelligent guy. You’re such a brainiac.”

Use flirty questions to loosen him up.

Keep it lighthearted and fun to ease the tension and get him talking. Ask questions to keep the conversation moving. Inject some playful teasing and flirting into your questions so he opens up and feels comfortable talking to you, which may make him more likely to want to spend more time with you. Try asking, “How are you single? Don’t get me wrong, I’m not complaining. It means people like me might have a chance. But how come you’re not in a relationship?” You could also try, “What’s your family like? Got any rich uncles I should know about so I can start scheming now?”

Tell him you should hang out to gauge his interest.

Talk about it hypothetically to see how he feels. Bring up the idea of hanging out without actually asking and see how he reacts. If he’s really open to the idea, great! It’ll be super easy for you to follow up and ask him. If he’s not super into it, you can just back off without having risked putting yourself out there completely. Try texting, “We should get together sometime!” or keep it more casual with something like, “Dude, we have to hang out someday.” You could also try, “We should grab dinner sometime” or “I haven’t been to the movies in forever! Let’s go someday.” If he reacts sort of neutrally and isn’t super for or against the idea of hanging out, no worries. You may still be able to ask him without getting rejected.

Ask about his availability.

Find out when he’s free before you ask him to hang out. If you already have plans or an event in mind that you want to ask him to come to, ask if he’s free on that day and time. If you’re trying to make plans with him, find out his general availability so it’ll be easier to ask him to hang out when you know he’s free. For instance, you could ask, “Are you busy Friday night around 7?” or “What are you up to this weekend? Got any plans?”

Choose something specific to invite him to.

He may be more likely to agree to it. Avoid asking him to hang out in vague terms or he might be more likely to turn you down or half-heartedly commit to the idea (and he might not follow through). Instead, have a specific event or location in mind when you ask and he might be more down for it. For example, say, “Hey, do you want to check out the new Italian restaurant with me on Friday” instead of “Hey, do you want to grab dinner sometime?” You could also try, “I was going to go to the art exhibit that’s in town right now. Wanna come with?”

Say you need a wingman.

Make him feel like you need his help. If you really just want to hang out as friends, ask him to join you as a wingman who can help you navigate a bar, party, or even a single’s event. Even if you maybe like him as more than a friend, it could make him more attracted to you if you enlist his help in a non-romantic way. You could try, “Hey, I’ve got this work party I have to go to, do you wanna be my wingman for it?” You could also try, “There’s a single’s night at this club I want to go to. Will you be my wingman for it?”

Include him in your current plans.

Ask him to join you if you already have something to do. Make the ask less awkward by talking about your existing plans and inviting them to come along with you. It’ll feel more natural and he just might be more willing to join. For instance, you could try, “Hey, I’m having some friends over to watch the Olympics this weekend. Feel free to join us!” You could also try, “There’s a free yoga class at the park this Saturday that I’m going to. You should come with me!”

Invite him out for drinks with some friends.

He may be more likely to come if there are other people. Asking a guy to come hang out with you alone could be a little intimidating for him. Tell him you’re going somewhere with some friends and it may feel more casual and fun, which could make him more likely to say yes. It’ll also be no big deal if he can’t make it—you can just go have fun with your friends! Try, “Hey! A bunch of us are going to grab some pizza and drinks this Friday night. You wanna come?” You could also text, “Some friends invited me out to an EDM show. Wanna tag along with us?”

Ask if he wants to grab coffee or lunch.

Keep it casual and low-pressure. If you really just want to hang out as a friend or if you’re worried he might say no to a night-time invite, try asking him to get together during the day. Suggest a coffee shop or a tasty lunch spot for an easy option that he may be more likely to agree to—who doesn’t like lunch or coffee? Try, “Hey, I’m starving. Wanna grab some lunch?” or “I’d kill for a coffee right now. You want to hit that new cafe with me?”

Frame your question as an offer to hang out.

Make it seem like he has a chance to spend time with you. Make yourself the prize that he can potentially win by putting the ball in his court whenever you ask him to hang out. Turn the offer around so that he gets a chance to hang out with you rather than you asking if he wants to see you. He may be more intrigued and likely to agree! For instance, try asking “Oh, by the way, I’m going to the museum in the city this weekend. Feel free to join” instead of, “Do you want to go to the museum with me this weekend?”

Give him an easy out if you want less pressure.

Make it easy for him to say no so he doesn’t feel obligated. If you’re really worried about him turning you down, or you don’t want to make him feel like he has to agree to hang out with you, give him the option to say no without any consequences. Tell him it’s totally cool if he can’t make it. He may say yes, he may say no, but you managed to ask him! You could try, “I’m going to see the new Marvel movie sometime this weekend if you want to come. No worries if not!” You could also try, “Hey, feel free to say no, but I’m going to 80s night at this bar tonight if you wanna join!”

Text him less after he agrees.

Avoid sending a ton of messages or it could turn him off. Resist the temptation to follow up with a bunch of texts once he says yes. Hang back and just wait until you get to see him. Congrats, you’ve done it! Don’t mess it up by blowing up his phone and you’re golden. If he says no, don’t worry about it. He may change his mind in the future or he could be busy. Things may change in the future.