So you want to ask out one of your friends and you’re extremely nervous about it. With good reason! Asking a stranger out is scary enough. Asking a friend out is a bit like walking through a dark wood that you know is chock-full of murderers — it's full of scary possibilities. What if they say no? What if they laugh at you? What if they say no and get weird about it and oh no, now the whole friendship is ruined and it’s your fault and you’re going to lie awake at 3 a.m. on cold nights thinking about it, forever.
Don’t worry. As with everything in life, there’s a way to navigate this with grace. Here’s a few handy tips on how to ask out that friend you like — without getting murdered or worse still, embarrassing yourself:
1. Make Sure Your Feelings Are Real
Yeah, yeah, we get it, your friend Joan has great teeth and you both laugh at the same BoJack Horseman scenes. But are you sure you like her in a I-want-to-create-a-small-person-with-you way?
Feelings are small and pesky and easily confused with other things, like noticing that your friend is attractive. Noticing that your friend is attractive is entirely normal and doesn’t mean anything. (All it means is that you’re a human with eyeballs.) Don’t go for it unless you’re sure it’s The Real Thing.
2. Test The Waters
Let’s say you’re hanging out with Joan and all her friends and she’s all dressed up. There’s nothing wrong with giving her a small compliment in a private moment. Something like “Wow, Joan, your teeth look AMAZING today. Who’s your dentist?” (OK, we can workshop this compliment.)
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You get my drift. Ease into it. See how receptive she is and if she flirts back with you. This has two great benefits: A) It’ll make you more confident when you actually take the plunge; and B) It’ll give her a hint of what to expect. Nobody reacts well to an ambush. Not even a romantic one.
3. Talk To Mutual Friends
Asking out somebody in your friend group is always going to be tricky. Your friends are entirely within their rights to have mixed feelings on it. After all, they’re going to be caught in the crossfire when things get weird.
One thing you can do to make it easier is to be honest with your friends about what’s going on. (And remember, if you don’t tell them you asked her out, she might.)
PLUS, if you tell them, they might have some useful advice to offer. Like the fact that Joan hates pit bulls, because she was bitten by one in the sixth grade. See, you didn’t know that before. Now you two can bond over how scary pit bulls are.
4. Show Her A Different Side Of You
If you only hang out with Joan at the local sports bar on Thursday nights, mix it up. I’m not saying that making dick jokes and eating hot wings with 9 other people isn’t the best way to showcase your attractiveness, buuuuuut it might be wise to explore other avenues.
Attraction requires effort sometimes. You wouldn’t show up to a first date in crocs, would you? (Would you? OK, we need to talk about this. Meet me out back. I’m very disappointed in you.) No, you probably get all dressed up, slick on the cologne you paid too much money for, and show up ready to wow her with your attentiveness and good manners.
It’s time to show Joan that you have more to offer than dick jokes and a shirt covered in ranch dressing. Offer her an extra ticket to a gallery or show or synchronized swimming contest and let her see that other side.
5. Timing, Timing, Timing
Joan got out of a bad relationship last week? Don’t ask her out.
Joan says she’s swearing off dating? Don’t ask her out.
Joan just took off her mask to reveal that she’s actually a swarm of bees disguised as a person? Well, then, definitely don’t ask her out.
In all seriousness, make sure the time is right before you go for it. Don’t sabotage your chances because you’re impatient. She won’t go on a date with you if she doesn’t want to go on a date at all.
6. Don’t Make It About Sex
It frequently happens in the movies that two friends share an adult beverage and end up Doing It. After which they go through a series of misunderstandings, grow distant, and then live happily ever after.
Well, real life is the same. Minus the happily ever after part.
It’s incredibly difficult to navigate a friendship into romantic territory as it is. Propositioning her for sex makes that about 88 times more difficult/creepy, and it’s not something a friend does. (Seriously. Look it up in the dictionary.)
How about this: when you’re drunk and horny, text your dog instead. You’ll never regret drunk texting your dog.
7. Be Clear About What You Want
Restrain the urge to be jokey about it. Maybe you want to mumble, "HeywannahangoutwithmeFridayhahaI’mkiddinglol" at her and then run away, but that’s what we in the biz call “sending mixed signals.” If she thinks you’re joking, there’s a good chance she’ll laugh and brush it off. You want her to take you seriously, don’t you? So you have to get serious. As serious as a house fire.
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Sorta like: “Hey, Joan. I know we’re friends, but lately I’ve been feeling something more for you. I’d love to take you out on a date if you’d be interested.” Leave her in no doubt as to what you mean.
8. Respect Her Feelings, No Matter What
The thing about asking out a friend is that it can be a jarring experience for the friend. She might wonder: “Was he only pretending to be my friend to get in my pants?” or any number of other unpleasant things.
Listen to and prioritize her feelings. Make it clear that this is a zero-pressure situation, and that you value your friendship with her above all else. If she gives you the slightest hint that she’s not into it, drop it. Remember, you were friends first. If you don’t respect her ‘No’, or act weird about it, you’re basically pissing on the friendship. So don’t do that. Look the awkwardness in the eye and deal with it. Put on your adult hat and put your ego aside and you and Joan will be just fine. Good luck!