How to Ask Someone Out.

Oct 10, 2021

I know we’re all thinking about how nerve-wracking it is when you’re ready to ask someone out. Your palms get all sweaty, you can’t think straight, and your armpits smell like onions that have been roasting in the sun all day… Wait, is that just me? I surely hope not. 

You guys, I get physically ill when I have to do things like that. If you’re the same way or just need to know how to ask someone out because how the hell are you supposed to know, this article is just what you need. So continue on, don’t skip any parts, and figure out how to ask someone out without totally freaking out.

How Long Should you Wait to Ask Someone Out?

Well, do you know? How long should you wait to ask someone out? That’s the first step before even asking them out, right? To me, it kind of just seems specific to each situation. It’s sometimes just as simple as knowing. If you know them well enough and you’ve both been digging each other’s energy the last few days or weeks, it’s totally the right time.

You just have to read the room, which is a lot easier said than done. Are they interested in you? Do they give you the same effort as you put in? Have they mentioned wanting to hang out soon? Yes? Then it’s a perfect time, no matter how long you’ve known them… As long as the scenario is safe, that is. 

For those of us that still aren’t sure and struggle with reading the other person, which is totally OK, here’s a better time frame for you. In more practical terms, the best time to ask someone out is between one and two weeks, but that fact only applies to certain situations. I think you know yourself and your potential date well enough to figure out when to ask. Just don’t overextend the waiting period. If you wait too long, they might think you just want to be friends or talking buddies rather than their next lover. Let’s not forget about the free time that opens up for them to go out with other people. Long story short, don’t wait too long to pop the question. Go after what you want, in a not-so-aggressive way

how to ask someone out

How to Ask Someone out in a Cute Way

You waited for the perfect time to ask them out, but now you’re stuck on how to do it and what the hell to do on the date. In my other article, “How to Ask Someone Out Over Text”, I list off a few cute date ideas that could be applied to this situation as well. So if you haven’t given it a read, you need to, obviously. 

You were fumbling on how to ask someone out, but now you need to know how to ask someone out in a cute way… come on, get a little creative, my friend. If you didn’t already know or don’t like to feel this way yourself, let me let you in on a little secret. People like to feel special, important, and to be complemented with a cute compliment.  

It’s hard to argue with that, am I right? Those three things should get your brain turning and thinking of ways to do the deed in a thoughtful way. Put time into your idea; I’m not saying buy some fireworks and make a production out of it… unless you have the money for that, then you should probably know I’m single and actively searching for a partner, kidding… or am I… 

Just make the idea and the date itself a little more than the last four dates they went on. Make yourself stand out, be the best version of yourself. Use compliments to knock off the compliment factor. Explain to them how much you enjoy your conversations and would love to continue in person. Plan out the date, have a list of ideas to choose from, or go above and beyond with it and arrange and make reservations. Maybe they’ve always wanted to take a pottery class. Well, look around and find a beginner’s pottery-making class for you guys to go to!

Make their words and the conversations you’ve had mean more (which, by the way, means that you need to practice effective listening). Show them you were listening, and you want to get to know them even more. Now that I’ve explained it, in a way that makes sense to me, not all- here are some things to keep in mind when you’re thinking about how to ask someone out and how to ask someone out in a cute way.

how to ask someone out in a cute way
  • Be Specific: After you ask them what they’re doing for the weekend, hoping they say not much. Ask, “Would you like to go to the new bar and grill in town and then stop by the concert that’s happening in the park?” This keeps your potential date aware that you are, in fact, asking them on a date, and there won’t be a group of friends tagging along.
  • Keep it Safe: Keeping it safe would be making sure you ask them on a date that helps you guys get to know each other more. Avoid asking them out to see a movie, as this makes it difficult to talk and engage with each other… Which is why you want to go in the first place, duh! Instead, try asking them out for coffee, lunch, dinner. Or get a little fun with it and ask them to go on a hike with a picnic, the beach with some wine, or check out a kombucha bar… If you don’t know what that is, do a little research. It could be right up your alley. 
  • Keep it Cool: We already know you’re the coolest cat on the block… and the hottest lol, so now it’s time to make sure you prove it. When I say keep it cool, I mean don’t sell yourself. You shouldn’t have to beg someone or convince them to come out with you. That comes off aggressive, pushy, and unattractive. You have feelings and took a lot of time to plan the date… because you took my advice, right? Right. So remember that. It’s OK if they say no. It might not be the right time or the right person. They’ll come along, don’t worry. Just keep doing you and being thoughtful and genuine.
  • Be Flexible: Wink, Wink… Oh my god, totally kidding. Save the flexibility and sex toys for down the road, eh? We’re not talking about the latest yoga position you’ve been practicing. Make sure you’re not dead set on the date you have in mind or the overall activity. Sometimes you might think your potential date would love to go to the new Italian restaurant in town, but it turns out they hate Italian, and you actually had no idea. Try reading their body language to figure out these quirks. They might offer up a new idea, and you should totally take it! Compromise always goes over well. It shows you’re up to changing things around and a go-with-the-flow kind of person—another super attractive characteristic. 

You’ve heard it all, not that my ideas and thoughts are better than someone else’s or your own. Just here to give you a new thinking perspective and ideas that you might not yet have thought of. Above is everything you need to know on how to ask someone out and how to do it in a cute way. To sum it all up, don’t wait too long to ask them out, but also make sure you know them well enough so that the situation is safe and comfortable. You know the right time. Be creative, thoughtful, and make them feel important. There’s no better way to do it. Good luck, you got this. 



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