Making the first move is something that used to be frowned upon by traditional dating rules. But times have obviously changed and you know it’s fine for you to approach someone you’re interested in and even—gasp—ask them out. But that doesn’t mean it’s any less terrifying. So if you’re wondering whether or not to go for it and how to do it without coming off as pushy, we’ve got you covered. Check out these seven times it’s perfectly acceptable to make the first move—and how to do it:
Giving Him Your Number
So you’ve been talking to this guy for an hour and he’s not really making the next move. Of course you can give your number first, and it doesn’t have to be one of those awkward um-here’s-my-card moments. “She can use a relevant topic as a way to subtly drop her digits,” says sex and relationship expert Emily Morse, host of the podcast Sex with Emily. For example, maybe you’ve been talking about the song currently playing; Morse suggests saying something like, “I can’t believe you’ve never listened to [insert musician’s name]! Go home and download their CD immediately and then call me to tell me how right I am about them. Here’s my number.”
Sending the First Online Message
If you’re wondering if it’s okay to contact that guy you’ve been eyeing on OkCupid, the answer is yes. But make sure to add some substance to your message. “Pick something specific from his dating profile page, Facebook, Instagram—wherever it is you are messaging him—and use that as a way to strike up conversation,” suggests Morse. By observing and pointing out something specific from his page (whether it’s a vacation he took or a hobby you have in common), it’ll set you aside from other women who just comment on his looks. And definitely don’t be shy about suggesting an IRL date after the first few messages. “The sooner you take the conversation out into the real world, the better,” advises Morse.
Asking Him Out
You know the traditional dating rules have evolved and so does he. So don’t be surprised if a guy is waiting on you to ask him out. The best time to do this is when the conversation is already flowing naturally, says Morse. “If you’re talking about how much you love sushi, tell him about the new place that just opened and casually drop, ‘You haven’t been? Well, we have to go.’” If he responds eagerly and interested, ask when he’s free. If he seems a little standoffish or vague, then you know he probably isn’t into it (and maybe unavailable), so you can move on without an actual rejection.
Making the First Call/Text
There’s absolutely no rule that says you can’t contact him first, especially if you’re calling or messaging to let him know you had a good time on your date, says Morse. It sends the message that you’re interested and want to go out again—and there’s nothing desperate about that. “Mention something that happened on the date that you enjoyed,” says relationship expert Diana Kirscher, Ph.D, bestselling author of Sealing the Deal: The Love Mentor’s Guide to Lasting Love. For instance, maybe you’ll mention the funny name of the beer he made you try or a joke he made. That way it can lead to further conversation (hopefully even a second date) and it’s not just your typical “thank you” text.
No matter what stereotypes tell us, men are just as confused as women when it comes to this, says Morse. She suggests going with your gut the moment it feels really right: Lean in, kiss him, then pull back a little to see his reaction. Just don’t be too aggressive and don’t ask if you can kiss him—that definitely kills the mood.
He might be just as cautious as you are about making the first move on the first sleepover, so don’t be afraid to take the reins if you want. If it’s clear that you’re both ready and interested, Morse says there’s nothing sexier than taking the initiative here, as long as you pay close attention to how he’s responding. “Test the waters before you throw it into full throttle,” says Morse. “While you’re making out, try gently leading him onto the nearest couch or bed, then climb on his lap and straddle him, while grinding your body against his.” Then you can pretty much seal the deal by whispering in his ear to ask if he has a condom.
Saying “I Love You”
If you really want to say it first, go for it—just know there are some risks involved. Kirschner warns that some men tend to be slower to realize they’re really in love or just more careful about dropping the words. So be prepared for the chance that you might not hear a reciprocation right away. Morse suggests going by the rule of three: “The first time you think it, let it marinate in your mind. The second time you think it, don’t say it, but imagine what it would feel like to say it out loud. How do you think he would react to it? The third time you think it, go ahead and tell him how you feel.” If that sounds terrifying but you still want to get that conversation moving, you may want to start with something like, “I’m really falling for you, I love being with you,” says Morse.
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