How To Ask If She’s Single (Without Making A Fool Of Yourself)
Picture this scenario: you’re at a party, you meet a beautiful woman, and you spend the entire evening talking to each other. You’re really hitting it off. You both like that one team! You’re both from small towns, and you both agree that wasabi peas are the perfect party snack. You want to marry her tomorrow.
There’s just one tiny problem. You don’t know whether she’s single or not.
There are some great context clues you should look for — like a wedding ring or frequent mentions of “My boyfriend says” – but let’s assume that you’re flying absolutely blind here and you have no mutual friends who would know. The only thing left to do is ask.
Having the “are you single?” conversation can feel extremely daunting, I know. That’s because it removes all plausible deniability. Hey, maybe you were chatting to her because she was next to the bowl of wasabi peas. With one question, you’re establishing that you have Romance on your mind. That’s scary!
There are no real rules about when to ask somebody if they’re single. Lots of people ask right off the bat:
You: Hi, I saw you from across the room and wow, you look stunning in that red dress. Do you have a boyfriend?
An approach this confident is not for the faint of heart! The problem with this opener is that it can lead to immediate rejection. She could say “Yes, and he’s the angry-looking 6’6 guy in the corner who’s built like a football player.” What a terrifying thought.
On the other hand, if you put it off too long, you’ll never catch that cute girl between boyfriends. It’s a real conundrum. But never fear- it can be done, and done smoothly. (Men have been asking women if they’re single for hundreds of years! You’re not alone.)
One way to minimise the awkwardness of a “No” is to volunteer information about your own status! A simple reference to your ex, or to your dating life, will likely elicit the same information.
You: I moved to the city a year ago, to live with my girlfriend. And then we broke up, so I’ve been struggling with online dating ever since.
Her: I know, isn’t it the worst? I’ve given up on online dating. My friends say I might as well be single.
Her: Oh wow. That sucks. I live with my boyfriend too! But we met through friends – I’ve never tried online dating.
Either way, the embarrassment is minimal, because you’re not asking her directly. But the beauty of this approach is also what makes it flawed. You could try this, but she may not give you the info because… she’s secretive due to her job as an international spy. OK, maybe she’s not a spy, but people don’t always volunteer information if you don’t ask for it.
Another, slightly more direct method is to comment on other couples in the room:
You: Wow, Tom invited a lot of couples, didn’t he? Check out that couple making out like teenagers! Reminds me of Facebook – it always makes me feel like I’m the only single person left in the world.
Her: I know! It’s the worst. I hate PDA. And yeah, I think I’m the last single person in my group of friends.
The safest bet is to laughingly mention something difficult about how you’re single, and then ask her if she can relate to it. This is more daring than the previous methods, but it’s still essentially casual – there’s a context for why you’re asking!
You: There’s this great Thai place around the corner. But it’s really hard to meet the delivery minimum because I live alone and I can’t eat that much food. Ugh. It’s discrimination against single people! I don’t know if you’re dating someone but if you are, check it out-you can order two entrées.
Her: *laughs* Oh, I’m not single! Thanks for the tip though, I’ll definitely tell my boyfriend about it. He loves Thai.
If you do go the direct route, and pop the scary S question, you have to be prepared for whatever answer you might get. This is (and I cannot emphasize this enough) crucial. Asking if someone is single isn’t offensive, but not handling rejection with grace certainly is.
You: I was wondering whether you’re single.
Her: Actually, I have a boyfriend.
You: Of course you do! He’s a lucky guy. Well, enjoy your evening.
Smile, keep it light, walk away. Women feel awkward too! You want to make the interaction as painless as possible for both parties. A nice compliment will improve her day, while showing her that this isn’t a big deal. Don’t make rejection into a big deal: there’s plenty of other women in the world who are single.
Of course, there’s a chance she is single, but not interested. Don’t assume that if she doesn’t have a partner, she has to be interested in you. Maybe you’re not her type. Maybe she likes women! Maybe she’s not looking to date right now because she’s about to move to another country. Whatever she says, be easygoing about it:
Her: I’m single, but I’m not interested, thanks.
You: Well, I wasn’t going to ask you out, anyway. Don’t flatter yourself.
Oh, boy. This is the worst thing you could do. Even if it’s true – you only asked about her relationship status because you wanted to know for a census you were taking – it’s the natural assumption to make. If you try and act as if you were never interested, you come off as somebody who’s lying, which is pathetic. It’s much better to gracefully bring the conversation to a halt.
Her: I’m single, but I’m not interested, thanks.
You: No worries. I’d be kicking myself if I didn’t ask! Have a nice night.
And once again, smile, joke, walk away. No big deal, right?
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But say that’s not what happens. Good things do happen! There’s a definite chance that the pretty girl you met is single, and even better – that she’s open to going on a date with you:
Her: Yeah, I’m single!
You: I’d love to take you to the Thai restaurant I mentioned, if you’re interested. You know, defeat their evil Anti-Singles agenda by teaming up.
Once you find out that she’s single, follow up right away! (Or the guy eavesdropping on the conversation is going to ask her first.) What’s the point of doing all the hard work if you walk away at the eleventh hour? Good luck, and congratulations on your new life, in which you are always able to ask a girl casually if she’s single.