Asking a stranger on a date? It's the most simple and simultaneously the most impossible task in the world. It's why online dating has proliferated — it's so much easier to approach someone in a formal "everyone is here to get a date" situation than in regular life. And I'm not knocking online dating here, but the odds are that while we often hear that almost one-third of couples met on online dating sites, that means that the rest of us — over two-thirds — are still meeting IRL (that's in real life). That means you might end up meeting your beloved in any random social situation. But how do you go from "Wow, that guy/girl seems awesome; I want to go out with them" to actually going out with them?
It's always an advantage to be a very attractive person, but no matter who you are — however gorgeous you look and how successful you are — it's easy to get the signals wrong. I mean, if Nicole Kidman has trouble picking up a man (see the hilariously awkward video below of her failed attempt to interest Jimmy Kimmel), that means we all screw up sometimes. And that's OK.
But there are ways to improve the odds. Whether you're young or old, gay or straight, recently dating again or long-single, the following expert advice will stand you in good stead.
Rock the small talk: Almost nobody is born being good at making small talk. For most of us, it's just plain weird; being friendly, open and affable with someone you don't know at all. But it's key to many life interactions, including meeting people you'd probably like to date. The only way to get good at it (if you are not naturally gifted in this area) is practice. Ideally practice first with people other than those you'd like to date. Always have two or three topics you can turn to for conversation starters, and remember, it's really about making the other person feel at ease. Since people generally love talking about themselves, that's always a good topic of conversation. As Slate's Gentleman Scholar Troy Patterson advises:
"To win a friend — or, at the very least, to gather data that will enrich your appreciation of the human comedy — you should ask something like 'What are you excited about?' — which is nice and wide and cheerful. To say, 'What are you looking forward to this fall?' invites the other party to remark on enthusiasms and travel plans and hopes and dreams, and it allows him his choice of a momentous or delightfully trivial answer. ... It will be your duty, in this joint improvisation, to ask good follow-up questions. It will be your pleasure to reveal something of yourself — the slant of your curiosity, the cast of your mind — by drawing him out and encouraging a self-portrait. Remember: Within many a superficially boring person, there is an interesting person waiting, all too patiently, to get out."
Introduce yourself: If you are in a public situation, it can be hard to gauge someone's availability or interest. The best course of action is simply introducing yourself to them, according to Mario at Ask Men (for whom this worked). Literally just, "Hi, I'm Jane, what's your name?" is a perfectly fine way to approach a stranger, and nobody can get offended by it because it's the opposite of weird or sleazy. If they don't want to talk, they will probably make it pretty obvious (and don't push it if they're not into you). In fact, b prepared for them to not be interested. (Them's the breaks when you're approaching a random person who could end up being nice-but-boring, could be coupled, could be having a terrible day, or could be your future spouse.) If they are in the midst of a grocery run, or a set at the gym, or they're sitting next to you on a flight, you should be able to tell just by the way they answer your first question if they are interested in speaking with you further.
Enlist a friend: When I spotted my current partner (we'll be celebrating five years together in a couple months), it was at a bar-birthday celebration for a mutual friend, but he was ensconced in a booth with a group of his friends — I definitely didn't have the guts to just walk up and start chatting with the group, and it seemed like they were old friends. I thought about interrupting him when he walked back from the bathroom, but I got distracted and ended up hanging out at another table. A few days later, I recalled that cute guy and asked my friend about him. She gave me his details (which made him sound even more awesome than just the visual I had gotten) and emailed his good friend about setting us up. Our two friends made the arrangements for our first date (and came along — it was a group thing); we didn't have to do very much at all except show up. We totally hit it off, but if we hadn't, it wouldn't have been a big deal either, since we were both there with our friends. Easy, fun for our friends (they enjoyed putting it all together) and low-stress for us. Perfect.
Keep it simple: You don't have to think of anything elaborate to ask someone for a date, and it doesn't have to be a big deal. If the simple intro suggestion above seems to be going well, just ask if they want to get a cup of coffee — or tea. (Repeat: Asking someone for 15 minutes of their time, which is essentially what a coffee date is, is NOT a big deal; you spend more time with the guy who installs your new washer, or anytime you go to the bank for any transaction that's beyond a teller's capacity). Think of a couple really fun, topical things to talk about beforehand, and ask them about themselves during the time you get together. Date done. You don't know if you are going to like someone before you date them anyway, so why make a big deal about whether it will work or not?
Or, make it elaborate fun: Over at Reddit, there's a great thread on all the coolest ways people have been asked out that have worked in real life! There are some very over-the-top date ideas there, many of which were put together to woo a specific person the dater was interested in and already knew. If you are in this boat of wanting to date someone who isn't a stranger, you might take some inspiration from ways to make the date request specific to that person and yet still give them a comfortable out if they want to say no.
If you strike out, remember the video above. If Nicole Kidman makes a mistake picking someone up (the worst kind, which is that Kimmel didn't even know she was interested), you might too. And it's really not a big deal.
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