14 Signs You Should Ask Him Out

Sometimes, this really sad thing happens where two people like each other but they're both too scared to make a move, and then they get old and die. Prevent this from happening to you by asking him out. Here's how you know you should.

Ask Him Out
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1. You want to tell him about the littlest, dumbest sh*t that happens during your day. And I mean dumb. Like, "There were free bagels at work today!" or, "They have a new Crunchwrap Supreme at Taco Bell!" or, "I used special stuff to make my hair shiny today!" dumb.

2. You're super-comfortable with him. You don't have that pukey feeling you have when you're on a date with George Q. Random from Tinder and you haven't even gotten apps yet and you already know it's wrong. You know?

3. It's hard work not to make out in public. Even though you haven't transitioned your relationship into a romantic one (yet!), you are finding it increasingly difficult not to tenderly Lifetime Channel For Women-style face-touch him.

4. He makes you laugh. Like you're going to pee yourself.

5. He's almost asked you a few times but lost his nerve — or he's asked you out on ambiguous "friend dates." You're 99 percent sure he's into you, but he's afraid of sticking his neck out. If you want to go out with him, just do it! It's not so bad. It's like jumping into a cold lake. You do it, and a second later it feels fine, and then you get seaweed on your breast.

6. You've mentioned other guys in front of him. If a girl has talked about her love life with a guy who's into her, it can throw him off. He thinks she just thinks of him as a nonsexual being, like a chair that happens to be an awesome listener.

7. You haven't been able to make a tipsy makeout session happen, for whatever reason. Maybe he doesn't drink. Maybe you don't drink. Maybe you've both time-traveled back to the Prohibition era. For whatever reason, the drunken makeout — the easiest way to transition friendship to more — has Not Occurred. No reason to wait for that to happen if it's not happening naturally. Just ask him out!

8. You work his name into totally unrelated conversations. "You know who else drinks water? Mike!"

9. You've progressed to texting. And it's the kind of nonstop text banter where you're distracted at work and keep looking at your phone and giggling.

10. You've already planned a date with him in your head. Start at the Vietnamese sandwich place you both like, go see the new Coen Brothers movie, and end up in bed. All you have to do now is make it happen.

11. You compare all the guys to him while watching The Bachelorette. If Mike were a contestant on a reality show to win the heart of a woman, he really would be there for the right reasons!

12. It's #empowering. Sounds corny, but actually being proactive and going after what you want, as a woman, feels great. Think of it as a Lean In lifestyle for who you're gonna make out with.

13. It's a good way to find out if a guy is super-heteronormative, closed-minded, or not into people who like him back. If he thinks that you asking him out is "desperate," it wasn't gonna work anyway. Homeboy needs to grow up.

14. You want to. Just do it! Worst-case scenario, he says no, and then condescendingly asks for a hug, not that that actually happened to an actual person who writes for Cosmo or anything. You'll be better for it.


Yes, You Should Totally Ask Him Out

How to Ask a Guy Out

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Anna Breslaw

Writer. Things I appreciate: Ghosts, white wine, men who look like they could protect me from predators, and a great homemade deviled egg. Also, I have a VERY ambivalent obsession with Sex and The City but I'm not like any of them, other than maybe Miranda's cat.