How To Ask The Person You're Casually Dating To Hang Again If They Haven't Asked You

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Spending time with a new special someone is always super fun. The early stages of budding relationships can also end up being totally anxiety-inducing — especially if you're not quite sure where their head is at. After a particularly enjoyable date, it can feel like a bit of a disappointment if the person you're casually seeing doesn't immediately ask you to hang out again. Luckily, we live in the 21st century, making it acceptable for you to make the next move by figuring out how to ask a guy to hang out again.

Despite popular belief, many men don't necessarily feel like it's completely up to them to pursue a new romantic interest, leaving the perfect window of opportunity for you to put some of your own seductive magic to work. If the apple of your eye is a lady, don't worry;  regardless of gender, most people like being pursued by someone they're interested in.

The key to keeping things on track in the early stages of dating is to get into a push-pull rhythm where neither one of you feels like they're doing all the heavy lifting when it comes to planning and arranging how to best spend time together. This can be a bit tricky if things are still very casual, and it's totally natural to be concerned about coming off too eager. But, like I said, anyone who's interested in buying what you're selling will be totally pumped that you like them enough to put yourself out there.

1. Start By Feeling Things Out

In my opinion, the main thing that keeps people from pursuing those they're interested in is the fear of being rejected, and this is completely normal. The best way to deal with this is to put out a feeler before you decide to ask them on another date. Initiate some texting banter, which will usually give you some idea of their interest level. Start by sending something cute, like the followup to an inside joke one of you made or something that reminded you of them — although try your best to keep it light and fun, not overly sentimental.

I've also found that texting after work hours makes it a lot easier to get a natural back-and-forth rhythm going because both of you are less likely to get entangled in distractions. If they're not being super responsive then, this could be a sign that they may not be super interested.

Remember, by reaching out, you are also making it pretty easy for them to suggest another hang out, but if they are not willing to engage in any texting chatter, then it might be better to let things sit for a bit.

2. Slip In A Positive Comment About Your Last Date


If they've responded positively to your attempt at starting a conversation, at some point, try to slip in a something positive about your last date. Maybe you saw an interesting movie with them that has lingered in your mind. Maybe you just really enjoyed whatever it is you did together. Tell them. Not only is this a great way to signal interest, but bringing up something you experienced together, whether it be a particularly yummy meal or some dope live music, is also a sneaky way of presenting a bonding opportunity.

Assuming you both had fun, this gentle reminder will help them start associating those positive feelings with you. I mean, after all, who doesn't want to go on a date with someone they were really vibing with?

3. Zero In On Something They Mentioned They Liked Or Were Interested In


This is why it pays to really tune into what your date is saying during your hangouts instead of letting their attractiveness turn your brain to mush. Maybe they are super into punk rock or really love a certain food; come up with a date idea around those things. It's best to have a specific event or outing in mind before you reach out so you're armed and ready.

If you can't really think of anything they might like off the top of your head, it never hurts to invite them along to something you enjoy doing or something you've been looking forward to. Don't make it too formal like your best friend's birthday dinner; keep it casual. Maybe your favorite museum has a new exhibit or something. Try to get creative.

4. Pop The Question

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OK, so there are a couple of different ways to approach actually asking them if they want to hang out again. Which method you use usually just depends on how comfortable you are with the situation.

If you're pretty certain they are into you, then why not show them how confident you are with something like, "What are you up to this weekend? I'm planning on checking out this new exhibit at the Whitney. Want to join?" This two-fold question gives them the opportunity to either accept, decline, or make another proposition. It's direct, to-the-point and, based on their answer, you'll have a solid idea of where they're at. If they already have plans, but suggest another specific time they could meet up, then don't sweat it — they are being truthful and just had other plans. But do notice if they get wishy-washy and are reluctant to nail down a specific time for a next meeting. This could mean that they want to keep their options open, or aren't quite sure how they feel just yet.

If you're worried about taking the all in approach then you can also be a bit more nonchalant and simply suggest you hang out again sometime with a "Let me know what you're up to later this week. We should do something again soon :)." Not quite as pointed as the first approach, but it still signals interest and makes it clear that you're up for another date in the near future. The ball is totally in their court at this point, so there is no need to send a follow up text. If you hear from them great, then go from there; if not, then shake it off and keep on stepping.

Sometimes, whether or not someone is interested in going out again is less about them not liking you and more about timing. There are a ton of reasons that may be standing in the way of another date that are completely out of your control. Maybe their ex just came back into the picture, or they have a crazy workload,  or they just want to keep things super open. Either way, sometimes things just aren't meant to be, so don't sweat it.

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