10 Reasons To Just Bite The Bullet And Ask Them Out

A common dating “rule” is that women should never have to ask a guy out – that, if he is into them, he would have asked them out already. That a woman deserves to be courted, and that a worthy man will put in the necessary effort to win her over. It’s a good enough advice if you’re stuck on someone and you need a kick up the arse to move on. But I find it pretty much useless otherwise.

Yes, I have asked guys out.

Yes, none of these turned out into a relationship.

Yes, I still advise you to go for it.

If you like someone, ask them out. It’s not a gender thing, or an empowerment thing, it’s not playing games or trying to establish some sort of relationship pecking order. We’re adults, knowing what we want, asking honestly for it, and taking no for an answer is part of the deal.

1. Not everyone out there is straight or cis.

The rule to let men do the asking pretty much falls apart outside of a traditional heterosexual context. I’m not saying that everyone who is LGBTQUIA+ is great at communicating and setting expectations straight out of the gate (ahem) but it shows the future of the relationship does not depend solely on the person doing the asking.

2. If the other person is into you, they won’t care you initiated things.

“Well, I would have asked you out if you’d only waited five more months. Alas, my fair lady, your assertiveness has shriveled up my interest. Farewell!” Who talks like this? And more importantly, why would you want someone like that in your life? (It doesn’t matter if you’re casual friends or if you’re already hooking up. If both of you want the date, it doesn’t matter who suggests it.)

3. Being told ‘no’ is not the end of the world.

It may feel that way, the first few times, especially if you like to assess a situation before getting involved. But at the end of the day, they are just a person, same as you. After a while, the ‘no’ will stop being scary.

4. The longer you wait for them to make a move, the harder their rejection hits.

Having a big imagination sucks when you crush on someone, because you get invested quickly. When they don’t ask you out, you take it as confirmation of your worst fears about yourself, while simultaneously holding out hope that today, today is the day, they will make a move and it will all be worth it! It’s death by a thousand maybes. Rip the band-aid off and get some real information – by asking.

5. Waiting is overrated.

Even Cinderella had enough of patience, and got her hands dirty. As the popular meme says: she didn’t want a prince, she wanted a new dress and a night off.

6. No, but really: They’re just another person.

When someone I crushed on made a degrading, fat-shaming joke, I tried to process this with a friend by saying “(this guy) is 90% great.” 

Their response was “90% great, that’s a tall order!”

Turns out, just because we like somebody, that doesn’t make them a living saint. But that’s what happens if 90% of the information you have about their character comes from your own fantasies.

Being held up as a paragon of virtue is a lot of pressure before you even go for coffee. Hold off judgment until you actually know them a bit.

7. You’re not a receptacle, a statue, or a robot.

The trap of waiting to be asked is that you’re objectifying both the person you like and yourself. You cast them as Pygmalion and yourself as the statue that they bring to life through the magic of dating. If, for any reason they pass you up, it’s either because you’re unworthy or they are somehow mistaken (or both). That sucks. Worse, you might feel inclined to double the effort (and keep sleeping with them) in the hopes of “changing their minds”. Don’t. Please. You’re a human being, with feelings and agency and a life that will go on regardless of what this person does (fyi: Pygmalion is a jackass).

8. It doesn’t matter what kind of person you are.

Like I said, I have asked people out in the past, and nothing came of it. Not because I asked, but because we were a bad fit as romantic partners. I couldn’t see it at the time, because I was lost in my own fantasy version of the relationship, but time and distance have made that clear. It would not have worked out, and no amount of wishful thinking would change that.

9. You deserve to be cherished. You are not owed a relationship.

I may never find someone who is a good fit for me – same as anybody else. The only certain things in life are death and taxes. You can never be sure what will happen in a relationship straight out of the gate, but you can be honest with yourself about what you want. As a great agony aunt once said, be the cherisher and the cherished. Don’t let yourself be jerked around.

10. Clarity is its own reward.

The other person may say yes and you will go on to live happily ever after. They might say yes and you will come to discover they are not as awesome as you first thought. They might say no and you might find out, subsequently, that they were terrible. They might say no, and you are able to stay on friendly terms.

Whatever it is, you at least would have been clear about what you wanted, and they would have had a chance to say if they can give you that or not.

There’s no mind games, or uncertainty, or overthinking.

You’re just two people trying to figure out if you want the same things.