Just the prospect of asking someone out on a date is enough to put a lump in your throat and damp patches under your pits. And then actually working out the specifics… shiver.
But knowing the answers to a few key questions—How do you know if they’re interested in you? Do you ask in person or via text, call, or DM? And what exactly should you even say?—can help you approach the nerve-wracking situation with confidence. (Or, at least quash those butterflies in your stomach down for long enough to sputter out the all-important question.)
So, for your anxiety-quelling needs, we asked a couple of dating experts to break down exactly how to ask someone out.
Propose a date, time, and location
It’s not considered asking someone out until you actually throw out a specific date, time, and location, says Tammy Shaklee, LGBTQ+ relationship expert and founder of H4M Matchmaking. Open-ended suggestions like “we should hang out sometime” are way too broad, and chances are the “hangout” will never come to fruition.
But, if you say something like, “Do you want to go out for drinks Friday night at the bar down the street?” This gives the other person the opportunity to give you a direct answer.
Let go of the fear
If even the thought of asking someone out triggers a panic attack, start to shift your perspective of it. “When we have anxiety over a potential outcome or we’re feeling scared of rejection, it can really impact how or when we ask someone out,” says Tzlil Hertzberg, a couples therapist at MyTherapist New York. “We can come across as unsure and lacking confidence, which can end up causing the rejection we feared from the start.”
Of course, letting go of the fear is easier said than done, but just remember, “you can’t control the other person’s feelings,” Shaklee says. “All you can control are your own feelings.” So why waste your time pining over someone when you can just ask them out and find out if they’re interested? Save yourself the time and anxiety.
Hertzberg recommends practicing what you’re going to say beforehand so you feel a bit more prepared. No matter what you say, use a tone that conveys interest and deservedness, she says.
Invite them to a group activity
If you can’t muster up the confidence to just ask someone out directly or you’re not sure if they would say yes, you can also ease into it by inviting them to a group activity you’re already planning on doing, Shaklee says. This helps take some of the pressure off. If they show up, that means they’re interested, which will give you the needed confidence boost to invite them to do something one on one.
Plan a light and casual first date
Although romantic comedies would lead you to believe that you have to go big to impress someone on your first date by taking them to a fancy schmancy restaurant, Shaklee advices proposing something that’s way more laid-back. “When it’s a really dark, intimate, and expensive place, you see a lot of people celebrating their anniversary or their birthday,” Shaklee says. “It’s not a casual setting. It’s just too heavy for a first date. Keep it light. Keep it casual.”
So what exactly does light and casual mean? “Just drinks and appetizers,” Shaklee says. “No more than two drinks. No more than two hours. Short and sweet. You should walk away wanting to know more about them and them you.”
With online dating, cut to the chase
The goal of online dating is to actually get out there and meet people, as fun as endless swiping and messaging can be (sarcasm, folks), Shaklee says. So, when it comes to online dating, it’s better to ask someone out sooner—especially if a relationship is your end goal. There’s no need to waste time.
“Ideally, you should chat online a couple of times,” Shaklee says. “Then you meet face to face within two weeks. If they’re not willing to do that, then they’re not serious about a relationship. They’re probably talking to lots of people online and stringing them all along.” So if you’ve been DMing someone for months without any face-to-face interaction, it’s probably time to cut them loose.
Use your voice
While there is no right or wrong way to ask someone out, there’s something special about asking by voice, either in person, over the phone, or even via voicemail. You know, the old-school way humans used to connect. “Hearing a person’s voice sets them apart from everybody else they’re talking to online,” Shaklee says.
Flip your perspective on “no”
Okay, let’s say you ask someone out and they politely decline. Then what? “Be kind to yourself and don’t let it discourage you,” Hertzberg says. “Putting yourself out there is like a muscle—the more you exercise it, the easier the process becomes. Accept yourself no matter what and remember that you have more control over your reactions than you think.”
Shaklee agrees. It’s all about how you look at it. “Put a positive spin on it,” she says. “You should be thankful you didn’t waste your time. You should be thankful they didn’t string you along. You should be thankful they’re not playing games.”
Looking for more dating tips? Here, 8 women share the best advice they’ve ever received. And here’s how to make sure you’re sending the right vibes with your body language.
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