How would a guy feel if a woman asked him out?

I found a great question that, while not complex, makes for a great jumping off point when it comes to the question of who should ask who out in dating:


If I’m interested in a guy, I am going to ask him if he wants to go on a date or hang out sometime. How do you feel about this, especially if it would be the first time you did something together? I’ve always wondered.


I think it’s safe to say that for most people their attraction to you and their availability determine whether they might be interested in you. I don’t care what their gender is or what their sexual orientation might be, I feel confident saying that 9 times out of 10, if you ask someone out, and they’d normally be interested in you, it doesn’t matter if asking them out breaks any gendered dating norms. If someone is into you, they’ll appreciate being asked out by you.

I’ll take it a step further. I’m pretty confident in what the average straight guy’s dating experience is like. I can’t speak to every single man’s experience, but I’m sure that for the average straight man, they’ve done more asking out in their lives than they’ve been asked out. There are exceptions to every rule, but I’m guessing that most guys aren’t being pursued nearly as much as they do the pursuing. I’m not saying that every single straight guy will be receptive to being asked out by you, but I’m confident enough to say that for most guys, it’s a non-issue.

But enough about straight dudes and women, we don’t need to dwell on them. I would encourage everyone, no matter who you’re into, to take initiative to ask people out. If you do so respectfully, in settings where people wont feel uncomfortable if they decide to reject you (i.e. they’re your wait staff, they’re a coworker, you’re providing them with a service), in a way that doesn’t make them uncomfortable (non-consensual touching, pulling out your genitals and calling it flirting, etc.), you don’t have much to risk. If they’re not into you, you gain clarity and can move on. If they are into you, you took initiative and probably look more attractive in their eyes for it.

There’s nothing wrong with being afraid of rejection, but it will hold you back. I wouldn’t encourage someone to use fear as a motivator normally, but if you’re hell-bent on being motivated by fear, be afraid of missing out on someone because you wouldn’t take initiative. Trust me, I’ve been rejected plenty of times, and I’d do go back and get those rejections all over again if I had to if it meant I would miss out on the right person for me.

My advice to you, whether you’re a woman wondering if it’s okay to take the initiative to ask out a guy, if the roles are reversed, or any other combination of people of varying genders and sexual orientations is the same. If they’re into you, they’ll be into being asked out by you. There are some folks out there who might feel put off by your taking initiative, but they’re not the right ones for you if that’s their deal breaker. As long as you’re not putting someone in an uncomfortable position, abusing your power, or asking someone out who has already rejected you, I think you can and should take the initiative.

Take a chance, it might lead to something amazing.

Good Luck Out There


Also published on Medium.

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