How to Ask Her Out
Practical Advice to Convince That Girl You Like to Give You a Shot
A lot has changed in the dating world in just the past ten years. It wasn’t so long ago that a majority of couples met through friends, rather than on the internet or through an app. It wasn’t so long ago that the term “ghosting” conjured up visions of apparitions and haunted houses, not selfish singles disappearing from your life rather than having the courtesy of saying goodbye. Ten years ago, nobody spent their toilet-time swiping through the profiles of dozens or even hundreds of local singles, expanding the sweep of their search for long across an entire city.
Yes, the dating game has changed, but as the saying goes, “the more things change, the more they stay the same.” Some things, it seems, are timeless. Men are still expected to do the wooing, and women to sit back and either accept or reject a man’s advances, and that dynamic seems pretty darn indestructible.
You can moan about it or decry it as unfair all you want, but if you actually want to alleviate your loneliness and meet your special someone, at some point in time you’re going to have to work up the courage to ask someone out.
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Dating apps help, somewhat, in that you both have to pre-approve (so to speak) the other dater, and instead of doing it in person – where you might get laughed at or have a drink thrown in your face, in the absolute worst-case scenarios – you’re doing it digitally, where the worst that can happen is just having your offer declined. But they still don’t solve your cardinal problem, which is convincing another human being to take a shot on you.
To help make things at least a little easier on you, we consulted some dating experts— from therapists to coaches to psychologists — to figure out the best strategy for approaching another person with romantic intent. What follows won’t guarantee you a date with the person you’re asking out (nothing can!), but it will dramatically increase your chances of success.
Be Honest and Sincere
This might sound like advice your grandmother would give you, but that’s because your grandmother was probably a wise woman who knew what she was talking about.
Sincerity is a huge plus, particularly when so many people are deliberately fake, concocting false personas that they think will make them more attractive. In a dating world where so many people are trying to be something they’re not, there’s something refreshing about a person who has the courage to be himself.
Joshua Klapow, Ph.D, a clinical psychologist with great insights into human behavior, heartily endorses the sincere approach: “Asking someone on a date must start from a place of sincerity. The more you pile it on, the more you try to be smooth or slick the more the BS factor comes out and the less attractive you are.”
Great, now that you’re committed to sincerity, you're probably curious as to how you should convey that.
“Ask her out in a very honest way,” recommends Klapow. “Ask ‘I would love to learn more about you.’ Ask her out in a situation that offers her and you an exit if it’s not working. Don’t make the first date, dinner or a movie, or anything likely to run late. Make it easy, in daylight, and time-stamped. Lunch or coffee is the easiest.”
One of the reasons those date suggestions convey sincerity is that they actually force you to have a conversation with the other person. If you invite them to “Netflix and chill” or to cocktails at a loud, fancy bar, you might be communicating an interest, but it isn’t primarily in who they are, and that’s likely to make them doubt that you’re really interested in getting to know them.
“It’s all in the authenticity and intention," adds Klapow. "If that’s there, then the words will follow naturally. If the intentions are compromised or less than curious, it doesn't matter what you say. They will pick up on the creep factor.”
Be Big and Make Bold Moves
Asking someone out takes confidence, but there are still meek, passive ways of asking someone out, whether that be fumbling with your words or slouching your shoulders and conveying timidity and insecurity.
Take this advice from Tina B. Tessina, Ph.D, a psychotherapist and the author of Dr. Romance’s Guide to Finding Love Today: “Flirting is a way of communicating without words. There are lots of ‘attraction behaviors’ that influence people to respond positively. Your body language is the first place to start. Make sure you don't appear shut down and closed off, and don't get a leg or an arm between you and your new friend like a barrier. Don't cross your arms or hug yourself, as if you feel afraid. Relaxed, open posture is much more inviting.”
What she means is you might inadvertently be communicating something unattractive, like desperation or anxiety or insecurity, by doing something as seemingly mundane as your posture or your body language. If you expect people to respond positively to you, you need to put your best foot forward, so to speak. That means you should make yourself comfortable, calm and presentable — the kind of person people want to spend time with — and you’ll be amazed at how much more receptive people are to your flirting.
Always Have a Plan
You also need to be direct and concrete in your communication. Lots of people flirt for the sake of flirting, with only vague promises of actually following through on all of that flirtation with a date or a casual meetup.
That’s why Rachel DeAlto, Match’s Chief Dating Expert, counsels men to “be bold and have a plan!”
There’s a very big difference between an ambiguous promise of a future meetup and a fun idea proposed with enthusiasm and clarity. Or, as DeAlto put it to us, “‘I would love to take you out for drinks Friday’ is much more effective than ‘Let’s go out sometime.’”
The specificity of your proposal reinforces a sense of sincerity and boldness as you convey what you want while putting the ball in the other person’s court with a particular location and time.
As Klapow already pointed out, your plan shouldn’t be elaborate or overly expensive or time-consuming. You want to keep things light-hearted and relatively noncommittal, in the event that you both decide that the date isn’t going anywhere. It’s very easy to sit down for coffee for 15 minutes before calling it quits, assuming there’s no chemistry, or for an hour and 15 minutes, if there is, but it’s extremely difficult to walk out on dinner and a movie or a lengthy hiking trip.
If, on your casual first date, you both have a sense that things are going well and you’d like the chance to get to know each other better or for longer, then you can simply plan a second date right away, or extend the first one by switching venues. But the whole idea behind this casual date proposal is that it lowers the barrier enough to make it worth taking a chance on you. Once you’re on the date itself, though, it’s up to your winning personality and charm to make things work.
If you follow this advice, you might not instantly go from insecure and inexperienced to a suave, sophisticated charmer with the confidence to ask out every woman you’re interested in, but you will give yourself a much better chance of securing a date and getting to know another human being – and that’s what dating is really about.
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