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How to impress your crush on a date

By Cora Boyd

Stop us if you’ve ever done something like this before: When picking a venue for a date, you angle to go to the bar your cousin owns so you can get free pisco sours all night and look really well-connected. Or when your date orders the pad Thai, you speak at length about the time you drove a moped from Chiang Mai to Bangkok.

Wait, that didn’t get you a second date?

Trying too hard to impress is something any dater has done at least once. And we get it, you want your date to think you are indescribably awesome. But it turns out that what truly works in your favor doesn’t require a performing a backflip, rolling up in a Ferrari, or even ordering the most expensive wine on the menu. It’s simply a matter of showing you care.

1. Ask thoughtful questions.

“We often think that someone will be impressed based on what we share about ourselves,” says dating and love life coach Evin Rose. “But in reality, everyone just wants to feel like their date is actually interested in getting to know them.”

If you ask thoughtful questions, you’re (more) likely to get thoughtful responses. Going beyond the surface-level script of where someone is from and what they do shows that you’re interested in their individual opinions, motivations, and experiences.

“The amount of people who don’t ask questions on dates is wild to me,” says Johnny, 25. “I once went out with someone who spent two hours telling me about the office politics at their job. I could barely get a word in edgewise. There’s no way I’ll want to go out with someone again if they just talk about themselves the whole time.”

If you want to present outlandish hypotheticals and would-you-rathers, go for it. But even the simple tweak of asking more follow-up questions shows your date you care and also provides insight into who they are. Instead of asking them to list their interests and moving on, ask them what compels them about tarot reading and how long they’ve been teaching themselves HTML.

“It sounds simple, but this can actually make someone feel interesting and special, which is way more likely to get another date than just raffling off ‘impressive’ stats about yourself,” says Rose.

As some old man in a bar in New Orleans once said to me, if you want to be interesting, get interested.

2. Keep it real.

On a date, you want to put your best foot forward. But your actual foot, not an imaginary foot based on a mirage of smoke and mirrors. While you certainly want to take opportunities to highlight what’s cool and oh-so-dateable about you, you don’t have to pretend to be perfect, and you don’t have to adapt your behavior to what you think your date will be into.

“When you show up in a genuine way in the beginning, you will be that much more likely to make a stellar impression,” says Spyce, a love, sex, and empowerment coach.

If “Queer Eye” has taught us anything, it’s that confidence is everything. And owning your opinions, experiences, and successes as well as your challenges, shortcomings, and gaps in knowledge is confident as hell. If you don’t get their “Vanderpump Rules” reference, ask for more information. If you can’t remember where you read a particular statistic, say so. If you completely disagree with their assessment of the new Billie Eilish album, tell them why.

Being honest about what you know and believe gives your date the opportunity to get to know you for who you actually are, and it also might spark a healthy debate. You don’t need to go out of your way to be combative, but friendly disagreement can foster fun banter and create exciting tension. And if you’re not compatible, it’s better to know sooner rather than later.

3. Be courteous.

Putting care into your appearance, offering to pay for at least your part of the bill, filling someone’s water glass when you fill yours, and agreeing on a location that’s convenient for the other person are all gestures of courtesy and respect. These small behaviors demonstrate that you value your date’s time.

“Manners are one of the first things I notice on a date,” says Alex, 26. “I don’t care that much if they put their elbows on the table or which spoon they use or whatever, but I notice when they clearly care if I’m having a good time.” When you go to get another pale ale, ask your date if they want one too. If your date is getting blasted by an air vent, suggest moving to the other side of the restaurant. If you run into friends who your date doesn’t know, introduce them by name and make sure they feel included in the conversation.

A date is a preview of a potential relationship. Your date will notice if you want to help them feel comfortable, and it bodes well for what being with you long term might be like if you do. Don’t shoot yourself in the foot by forgetting these small courtesies and acting like you’re getting coffee with a colleague you don’t particularly like.

4. Take initiative.

If you’re into someone, you don’t have to pretend you’re not. Whether it’s asking them out, deciding where to meet, initiating a kiss, or following up about seeing each other again, taking decisive action is bold. And dating favors the bold.

In a dance where both parties are waiting on the other to make a move, don’t be afraid to go first. You’ll only come on too strong if you make move after move when the other person clearly isn’t reciprocating. Taking some initiative communicates to your date that you’re not expecting them to carry the weight of moving the relationship forward by themselves.

“I think a lot of young people are afraid of seeming too available,” says Simone, 26. “But I love it when someone takes initiative to hang out with me. It’s flattering when they set aside time and then follow through. It doesn’t make it seem like they don’t have anything else going on — it actually makes me feel like I’m a priority and that I can trust them to be accountable to me.”

5. Optimize for fun.

To state the obvious, most people will make the decision about whether to go on a second date based on whether they had a good time on the first one. So instead of opting for run-of-the-mill drinks or dinner, dating coach Ruby Le suggests choosing an activity that is flexible, casual, and fun. Think: a game of mini golf or visiting a neighborhood that’s unfamiliar to both of you. “Exploring allows you to show your spontaneous and adaptable side, and games allow you to show your competitive side.”

The best way to have fun with someone is to — drumroll please — be playful. Build a humorous rapport with your date by cracking jokes, laughing at theirs, making fun of each other a little bit, acting curious about them, taking the conversation into uncharted waters, or trying something neither of you have tried before. Fun is contagious, so the chances are high that if you’re enjoying yourself, they’re more likely to as well.

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