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6 ways to ask out your crush & 6 things to never do

Asking out your crush sure is awkward, and there’s definitely no easy way to do it, but there are some things to try or completely avoid.

Give them an actual plan

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The first thing to remember is that you want to be direct about what you want. Tell them exactly where you want to hang out and what you want, instead of putting the pressure on them. Be clear by asking them something like, ‘Do you want to go for a coffee on Saturday?’

Making clear plans makes it easier for them to say yes or suggest another day. It also gives them the chance to turn it down, too. That’s pretty important. The truth is, vague invitations create a lot more awkwardness than direct ones.

Pick a moment that already feels natural

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You don’t need to march over with a speech prepared when you’re asking them out. No, try asking them when you’re already talking to each other. The fact that you’re already in a conversation should make the whole thing a little easier.

There’s less pressure, for one, and it also gives them room to respond normally. Just remember that there’s no such thing as perfect timing, that doesn’t exist. But asking them on a date during a comfortable one-on-one chat is a little less awkward.

Leave the emotional weight at home

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Make sure you keep the invitation low-pressure. That means you don’t need to tell your crush your entire romantic backstory before they agree to a cup of coffee. It’s a lot to drop on somebody. Simply keep things light and give them space to decide.

They should be allowed to decide whether they actually want the date without also feeling responsible for you. You can always save the deeper stuff for later. You know, assuming there is a later, let’s hope that there is.

Make ‘no’ a completely usable answer

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There are some people who make rejection weird before it’s even happened. They’ll say things like, ‘Please don’t say no,’ and make jokes that they’ll be devastated. Don’t be like that. Give the other person an easy way to say no and let them know that, actually, it’s okay.

Try saying, ‘No worries if you’re not into it.’ That’ll let the other person know that their declining isn’t going to open a can of worms. An easy exit will make it all less tense, and that’s good news for you both, really. 

Cut out the middleman

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It does feel safer sending your friend over to find out what your crush thinks of you. But that doesn’t mean it’s a good idea, as it turns the date into more of a committee meeting. Ask your crush directly and cut out the middleman.

Three people don’t need to know about a conversation that only really involves two of them. Get the answer yourself, without any of the intensity. Nobody really liked playing telephone, anyway.

Pick up a thread you already started

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One really great strategy is to stay on-topic. Instead of asking them out in a random way, try bringing up the things they mentioned before. They said they like horror movies, so suggest going on a date to see one of the latest ones.

They mentioned liking tacos. Try inviting them on a date to the new Mexican restaurant.

Use the conversations you already had as the basis for your date because it shows you were actually listening. That always helps. Just make sure your intentions are clear, too, so that it doesn’t seem like friends hanging out. 

Lose the audience

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Now for the things to avoid.

One of the biggest mistakes people make is asking someone out in front of all their friends. It might make you look confident, yes, but put yourself in the other person’s shoes. Everyone’s watching to see your reaction.

A person who might’ve said yes privately will probably feel uncomfortable about giving any kind of answer, now that they have eyes on them. You really don’t want to put them in that position.

Take the first answer seriously

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‘No’ is a complete sentence. It’s not the start of negotiations, and it’s a full answer, so you have to accept that. Don’t be the kind of person who keeps asking because they think the answer might change. That just makes things uncomfortable pretty quickly.

They already know you’re interested, and they decided to turn you down. Newsflash, they’re allowed to do that. The only thing you’re doing by asking again and again is putting pressure on them. They’re not going to be interested in someone who does that.

Don’t send the director’s cut

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Your crush doesn’t need a huge paragraph explaining everything you feel and how you’ve been into them for six months. It’s just not fun. They won’t know how to respond properly, and they really don’t need all of those details.

Keep the first ask short and sweet. That doesn’t mean you can’t talk about your feelings, you totally can. But perhaps you should save that conversation for when things actually go somewhere, if they do.

Don’t translate ‘maybe’ into ‘yes’

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It’s weird how some people do Olympic-level mental gymnastics with the word ‘Maybe.’ They treat someone’s uncertainty as a sign that they’re only delaying the date. The doubter thinks there’s a chance they’ll get together.

There usually isn’t. Leave it alone when someone hasn’t actually agreed to go out with you, and take their uncertainty as what it is. Uncertainty. There’s really no need to try squeezing a yes out of an unclear answer.

Don’t trap someone behind the counter

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It’s true that the person working the register might genuinely be enjoying the conversation. It’s also true that they’ll get uncomfortable if you ask them out. Don’t put people in a weird position by asking them out while they’re stuck at work.

They’re not able to end the interaction easily. It’s the same issue for your coworkers, you don’t want them to be trapped in a situation next to you. It’s better to ask when they have some room to answer. You know, like a person, not an employee with a name tag.

Don’t hide what you’re actually proposing

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The most important thing to remember is that you shouldn’t ‘trick’ them into a date. That means don’t invite your crush to dinner while insisting that you’re just hanging out. You should both be on the same page.

There’s no need for a big announcement about romance or anything. Simply give them enough information to understand the invitation, and so that they know exactly what you’re asking them about. That’s not too hard.

Sources: Please see here for a complete listing of all sources that were consulted in the preparation of this article.

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