The Art Of Asking Someone Out: 9 Simple Habits Of People Who Always Get A Yes
Sofia Huerta | Unsplash Look, guys, we get it. We know you bear much of the burden of kicking off first dates. We get how hard it must be to approach a woman cold to express an interest in dating her or ask her out. We understand that nerves may get the best of you and you may not know how to approach or start a conversation with a girl, let alone how to get her to be your girlfriend, causing you to end up over- or understating your case at the moment of truth.
Generally speaking, I do appreciate that there is an element of bravery involved. And yes, it can be flattering as well. That having been said, when you approach us cold, we are keenly aware that your approach has to do with only one thing: how we look.
Spare me the comments about “energy” or “how she laughed” or “how she was with her kids.” I know that is what you might tell her, but she knows the truth … you like what she looks like. So this sets you off at a disadvantage for sure.
Because all we are going to know about you is how you look (far less important to women than men) and, therefore, much more importantly, how you choose to approach us. I thought that, based on my own and others’ experiences, I could set up a kind of guide of “hits” and “misses” when it comes to the art of the cold approach before a first date. Here are the most important tips you need to know about how to start dating the girl who catches your eye.
Here are 9 simple habits of people who always get a yes:
1. They don't ask someone out under the guise of 'helping out' with random tasks
I actually fell for this once, and it was very awkward when I realized too late that the gentleman in question had no interest in “doing business” with me except euphemistically. I guess maybe you think you are “putting the ball in our court,” but it is essentially dishonest, which is not a great start to anything.
Handing someone a business card under the guise of professional interest when your actual intentions are romantic is, let's be honest, a bait-and-switch. Research published in 2025 found that deception in romantic contexts often backfires, igniting conflict and damaging trust before the relationship even begins.
2. They don’t go from zero to 60
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When you go from being the-guy-behind-me-in-the-checkout-line to the-guy-who-is-offering-to-cook-me-dinner-at-his-place in the span of 5 minutes, you are not likely to get anywhere (or if you do, I am desperate and will soon be watching your place through binoculars). It’s fine to chat someone up and gauge if there is any interest, but tap on the brakes here.
3. They don’t make weird eye contact
This is a big one; I recently spent an entire meal out with friends with a guy at the bar staring at me so intently that instead of enjoying myself, I was in panic mode trying to figure out if I knew him. He waited until we were on the way out to make his move, at which point I was so stressed out by his weird attention that I’m sure I was rude. I’m not saying don’t try to make eye contact. I am saying don't stare!
Staring is defined as sustained eye contact exceeding typical conversational norms, which is generally around three to five seconds. Researchers observed that drivers at intersections actually took off more quickly when confronted with a persistent stare from onlookers because our instinct is quite literally to flee.
4. They don’t stalk people at work
Yes, we see you. No, we can’t leave, we are working. This feels like a teenagers-at-the-mall move, btw, not a grown man's behavior. I have heard a million variations on this theme, but I’m just going to bottom line it as a no-no. If a woman is interested in you, she’ll let you know. You don’t increase your chances by making her feel trapped by your attention.
5. They don’t oversell
Okay, you’ve approached, you are talking, it seems to be going okay. Do not tell us about your fancy car, your big bonus, or your vacation plans. It’s tacky and insulting; it assumes we are shallow and attracted to shallowness. If you are going to go with that angle, you are 100% responsible for ending up with the kind of women who value that over your character, frankly.
Research from the Journal of Positive Psychology found that both men and women are drawn to humble partners, and that narcissistic self-promotion becomes "extremely annoying" once you get past initial attraction.
6. They make light conversation first
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This is the lowest stakes way to see if she is interested. Is she making eye contact and answering in complete sentences? That is a good sign! Is she giving you “yes” and “no” answers and then looking away? That is a bad sign! Read the easy and obvious signs, please!
When people are disinterested, they give closed-ended answers and try to end the conversation. Studies on attraction show that receiving eye contact from someone predicts romantic interest, and direct gaze is associated with higher perceived likability and attractiveness.
7. They give them space
Close talking and premature touching are going to send the wrong signal. Having a relaxed, open-body language that is respectful of her space will make her feel safer and more comfortable.
Getting too close too fast literally triggers a danger response, not butterflies. Research on the study of how we use physical space confirms that people who manage space well and stand at a respectful distance are perceived as more confident, likable, and trustworthy.
8. They engage the people they're with
If she is with people, don’t zero in on her and exclude these people from your attention. It makes everybody (especially her) more at ease if you acknowledge reality and gives you a much easier exit strategy if her response indicates one is needed. However, if she turns you down, don't then ask her friend out. “Sloppy seconds” is not exactly starting off on a good note.
When you acknowledge everyone present, you're doing more than being polite; you're leveraging what social psychologists call social proof. Approaching people rather than individuals avoids awkwardness, and the presence of a friend can put less pressure on the interaction.
9. They pay them a sincere compliment
I'm a fan of compliments in general, even when not attached to flirting. Complimenting others not only boosts their mood, but it boosts yours as well. Even if she doesn’t want to go out with you, this will more than likely get you at least a smile, and that is always a step in the right direction, right?
Again, we are keenly aware that even if you are not “our type,” your (respectful) approach is a courageous act and should be responded to courteously. If you follow these guidelines and still get a rude response, then you just dodged a bullet.
As the old fairy tale says, you need to kiss a few frogs in your search for true love—just keep the kiss metaphoric until you have actually gone on a successful date, okay?
Kara Post-Kennedy is an editor and columnist at The Good Men Project; a blogger at Your New Best Friend and Huffington Post, and former Editor in Chief at OTV Magazine.
