Asking someone out is both the easiest and hardest thing in the world. No one likes getting shut down or rejected, but if “no” is the worst thing that can happen, then it can’t be that bad, right? It’s a matter of shooting your shot, and while the idea is easy, in practice, we can start to overthink and maybe get a little timid. So how do you go about shooting your shot with someone you might be interested in? 

Shooting your shot

1. Spitting game

You can’t just go up to a random person and ask them on a date out of the blue. That’s weird behavior. And spitting game isn’t as hard as most people think. Yes, some are better at it than others, but that’s true for any skill. But you need to remember one thing. The person you are talking to is just that, a person. They aren’t some scary alien who will eat you. Start up a conversation, be flirty and playful, and be yourself. If they aren’t interested, all you have to do is back off. 

And no, spitting games doesn’t just mean to use a cheesy pick-up line or compliment them randomly.  

2. Please don’t be vague

Being vague when asking someone out is how you end up on a date with someone who doesn’t know it’s a date. A phrase like “let’s hang out” is good but vague. Let the person know that you are interested by asking them on an actual date. Ask them to dinner or something along those lines. Make it clear that it is a date and not a platonic/friendly hangout.

So many times, people will tell you to go ask someone out, but it’s not helpful. Saying “hey, wanna go out sometime?” will lead to an empty conversation. Be specific. “Hey, do you wanna grab dinner on Friday? There’s this restaurant I’ve wanted to try out.” And if you don’t have a restaurant in mind, then look one up on google. And make a reservation if possible. (My app of choice is Resy.)

Maybe you don’t want to spend money on a meal. I can understand that I’m broke as heck, but that doesn’t mean you still can’t have a fun date.

Three random date ideas just for fun.

  • A museum – Most museums are pretty affordable and can be a great place to walk and talk and have a generally good time.
  • A picnic – Maybe you are a home cook who knows how to chef it up. A picnic in the park (weather permitting) can let you show off a little bit. 
  • Play pool at a bar – I know most pool bars look sketchy, but you can usually find a decent one in your city. And either you are good at the game and can teach them tips and tricks, or you can laugh about how bad you are together. 

3. Don’t fret

Worst case scenario, the person says no—big whoop. Rejection is a part of life. Not everyone wants to go out with you, and that’s no one’s fault. Don’t get caught up in the negative, and learn to move on and bounce back up. Don’t be the creep who can’t let it go. 

Better case scenario, they said no because they are busy on Friday, but they would still like to go out when you. This is great for you because it means they want to spend time with you even though Friday (per my example) didn’t work for them. 

Best case scenario, they said yes, and now you have a date for Friday night. 

4. Shooting your shot digital vs. IRL

Whether we like it or not, we live in two worlds, the digital and the real world. Asking someone out can differ depending on which avenue you take. If you’re asking someone out in person, then make sure to make eye contact when talking to them. And if it’s over text, you have probably been talking for a little bit which means you can be playful and flirty with how you word your text. Maybe you issue a challenge that they can’t beat you in mini-golf cause they were bragging about their putt skills. 

At the end of the day

Remember, dating is supposed to be fun, and while asking someone out can be nerve-racking, it should still be kind of fun too. And even though you’ve gotten through the hardest part by shooting your shot, now you have to get ready for your date, which is an entirely different monster. Pick clothes according to what you have planned. If it’s a museum, you can get away with something more casual but if it’s dinner, then maybe wear something with a collar. 

And when you have overthought all of that, you can start to overthink about all of the stuff you will talk about on your first date. But it’s okay cause we have you covered. So here are some things to keep in mind for first-date conversations. 


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