What to Do (and Not Do) When Asking Your Crush Out

By: Lina El Saie

Thinking of shooting your shot, huh? You see this person, you like them, and they might like you back? Or you think this person likes you back at the very least and you know them well enough to want to explore the possibility of a relationship based on your compatibility? Well, now you’re thinking of shooting your shot, right? But how? There is no one size fits all method for shooting your shot but there are a few things you could do (or not do) to make the process more enjoyable, or less stressful at the very least. Shooting your shot can be difficult because we often feel insecure and scared, but I genuinely hope this helps.

Make sure that this is what you want to do

Please, please, please do not ask someone out only to reject them the next day. It’s an a**hole move. If you’re thinking of shooting your shot, make sure that you want to ask this person out, that you want to make this commitment. You need to think about this seriously, people’s feelings, their thoughts, their bodies – aren’t yours. You’re entitled to no one. So, you to take a deep breath before approaching this person you like and being very clear about what kind of relationship you want with them. You must be honest about your expectations.

Surface-level interactions have no place here

For the love of God (or whatever you consider holy/sacred), get to know this person properly. None of the surface level bullsh*t is allowed in this house, please put in the effort. Get to know who they really are, in-depth. Ask questions, go deeper, repeat, or share a story, go deeper, repeat. It’s not about having conversations about your past or your parents or some sort of trauma-bonding (because admit it, we do that, all the damn time). You never know what a person is truly made of until you’ve been through absolute shit together. We all talk great about ourselves, but it’s in situations of hardship that we are honest in our actions as a reflection of who we are. So, because that’s impossible in the talking stage, try your best to be honest then. Don’t be afraid to ask difficult or sensitive questions, just ask that person if they’d like to answer or not, give them warnings, too. That’s really all you can do.

Make sure your values align

Upon the event where the feelings are reciprocated and they are down with the commitment, do you see yourself with this person? Is this the person you want to be with? The who we can get over our differences is bullsh*t, okay? You can’t be with a person who has completely different morals and ethics, without question. Some differences are fine, if they don’t like your favorite color, for example, but if you disagree on basic human rights, that is so beyond not okay. Take this one with a grain of salt, because if you can talk about it with them – in a civil manner – you should.

The How

There isn’t one way to ask a person out, someone might like a big gesture, but another person might not. It’s very important to understand what the other person likes (and what you also like). Asking a person out isn’t about pleasing them at your own expense, a relationship is a mutual endeavor, you both have to share feelings, you both have to put in the effort, you both have to invest time, and you both need to be safe and comfortable. It doesn’t have to be this big event, especially now during the second wave of the pandemic where life is hard as is and relationship-logistics suck a lot more than they usually do.

You can dress up for a facetime call and ask them to their face, nobody ever said you couldn’t send a “will you go out on a coffee date with me?” via text, and you certainly could go out somewhere open and green and have a cute picnic where you can ask or (cute, dramatic, Hallmark moment), have the question written out on a cake or cookie? A cute handwritten note would be adorable if the person is not 100% with the zoom/facetime or in person, too! You make them a playlist where the first word of every song says something special or cute and they could listen to it later if they commit to you. You could also have a virtual dinner date; the possibilities with this one are endless (social distancing and being in a different country or city should not stop you if it works for you and if you’re willing to put in the effort).

Again, these are just examples, maybe the person you want to ask out won’t like any of these or maybe they will, but please think this one through because this is important. You are allowed to feel sad but you are not allowed to invalidate or push their response if it’s a rejection.

Take a deep breath, they don’t owe you sh*t

Keep in mind that rejection is a possibility and while it will hurt either way, it’s probably not personal. Unless you know you can take a rejection, don’t shoot your shot, you’ll end up heartbroken. You might put in the effort and time and energy. You probably are a fantastic person. But rejections are so valid. Everyone has the right to choose, you can’t begrudge that a person or hold them accountable for something they chose that has nothing to do with you. Respect their feelings, please, and keep yourself safe.

Okay now that we’ve discussed what you should do, I think that it would be beneficial to discuss the things that we should avoid


We’re not in 7th grade anymore. I don’t think I need to elaborate, but in case I do have to elaborate lemme say this loud and clear: “t or d” is not the way to shoot your shot because it is literally a party game (fact check me I dare you). It’s also insensitive and puts people on the spot and is generally uncool. 

Do not get outsiders involved

This doesn’t mean that you shouldn’t take advice from your friends or that you shouldn’t ask their friends for help if you need some help. This is about not implanting a third person into an equation that has nothing to do with them. You can’t ask someone to ask your crush out for you facepalm. Try to eliminate having a “carrier” pigeon. A carrier pigeon is what I call that one friend who is friends with both of you and sort of ‘sets up’ the relationship for you (P.S it’s bullsh*t). This is such a bad idea, tbh, because you’re depending on someone to be the middleman instead of being upfront about things and trusting your crush and yourself and communicating.

Relying on someone to tell you what to do and when to do it and how to do it means that you don’t know them well enough to do most of this on your own; I say most because there are some things that you won’t know but you should know at the very least something. Including a carrier pigeon sort of creates this dependency on the carrier pigeon, like depending on the carrier pigeon to know what they like and what they don’t like instead of getting to know the person you want to ask out. Whilst there are things you can ask the person you want to ask out, there are some things you cannot and only then you should ask one of their friends, but a carrier pigeon or a middleman is a no go.

Do not take advantage of their vulnerability

If the person is vulnerable for whatever reason, whether it’s grief, heartbreak, loss, anger, or even self-loathing, they’re at a point where they’re not of ‘sound mind’ to make a decision that they truly be comfortable with. It’s such a d*ck move if you take advantage of them that way, pure manipulative and abusive behavior, but I know we’ve been taught that it’s okay, which is why I’m pointing out that it is not. Don’t be an a**, let them heal and let them feel okay again, you can wait, I promise.

More emphasis on emotional manipulation

Okay, you did everything you have to do from the beginning and it’s okay you could get rejected, that’s completely normal. It’s okay that’s completely normal, no one is obligated to reciprocate your feelings. Upon the event where you are rejected, you take the L, you do not guilt trip them, you do not blame them for rejecting you, do not try to make them feel bad for rejecting you. If this is how you react to the rejection you do not deserve this person, this person does not deserve your bullsh*t. If your first reaction to getting rejected is to try to manipulate the person, take a step back, apologize, and step down. If you cannot accept rejection do not shoot your shot.

Shooting your shot is hard, and congratulations you did it! I hope you were successful, if you were not I’m very sorry but you did your best it’s okay. These are just tips, feel free to tweak them depending on the persons’ preferences. Again there is no one size fits all to asking people out and hopefully, these tips will help. Remember that shooting your shot is hard, and you did it or you’re going to do it or you’re thinking of doing it. You got this, good luck.

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