How to Ask Someone Out: Expert Tips for Acting Like a Gentleman

Despite the fears of our inner middle-schooler, asking someone out doesn’t have to be sweat-inducing. With the right mindset and strategies, you can approach your long-time crush or stranger at the coffee shop or bar with a greater likelihood of getting digits and a date.

Here are tips from two of the most successful dating coaches in New York City. Nope, you won’t be negging anyone.

Note: The Manual’s is a men’s publication. Our advice is written with guys in mind but the tips can be useful to anyone.

Meet the Experts

Cher Gopman, dating coach and founder of NYC Wingwoman, is a former psychiatric registered nurse with experience working with men with histories of anxiety and divorce. As a female, she “brings down the walls guys have up around a girl and … helps good guys get into relationships where they’re happy,” Gopman tells The Manual.

Connell Barrett, founder and executive dating coach at Dating Transformation, works with men around the world to help them connect with women by being authentic.


Obviously, you have to approach someone to ask them out. If this terrifies you, circumvent the situation of crossing a crowded bar and sign up for a singles event. Gopman says these events are geared toward helping people meet and open up with icebreakers.

date couple beer brewery
Westend61/Getty Images

If you’re in public and see someone you want to ask out, begin by approaching them. Ironically, the easiest way to appear creepy is by watching from afar all night and doing nothing. When you approach, stand tall, make good eye contact, smile, and focus on your “vocal tonality,” Barrett says. “A strong, resonant tonality conveys confidence.”

Open with a Sincere Compliment

“The most important thing is to make her/them feel comfortable,” says Gopman. “Once you go over, compliment in a confident manner; don’t say it quietly or meekly.” The compliment shouldn’t be canned (please eliminate these pick-up lines).

“Many guys approach and flirt from a place of wanting something (a date, sex, an ego boost). When you shift toward giving the other person a good experience … the other person wants to give back.”

What catches your eye about them? Their energy, clothes, hair, laugh? “Maybe you notice their awesome leather jacket, quirky tattoo, or vintage Chuck Taylors,” Barrett says. “A good compliment is a form of giving. Many guys approach and flirt from a place of wanting something (a date, sex, an ego boost). When you shift toward giving the other person a good experience, things go better, and the other person wants to give back.”

Look at the person and compliment from the heart. Then go right into introducing yourself and ask a question about what brought them to that location, Gopman suggests.

Convey Your Interest

Barrett says the key to a successful approach is “the two C’s: clarity and charm. Clarity is about making it obvious why you’re breaking the ice. And charm is about being friendly, playful, and authentic … and being fine with whether or not you get a date.” The point of being clear and charming is to distinguish yourself from the majority of men who usually go to one of two extremes: sending unclear signals or acting too intense or “wolfish,” as Barrett says, “which can make the other person uncomfortable.”

When you approach, clearly convey your interest with either a compliment or something simple like, “Hi, I just saw you and had to meet you.” Crack a joke, be friendly and vulnerable, and pat yourself on the back for getting over the hardest part. “Any guy can swipe right on Tinder, but it takes courage to approach that person at the gym, at Whole Foods, in a bar — and that confidence can spark an instant connection,” Barrett says.

How to Know if They’re Interested

Before wasting your time and feeling bad about your efforts, check if they’re interested. Good signs include if they turn their body toward you; if they’re smiling, playing with their hair, licking their lips, laughing, asking questions; or if they’re touching you at all.

couple beer bar date

“If you’re having drinks and they place their glass between the two of you, that suggests there’s still an emotional barrier,” Barrett says. “If they move the glass off to the side, they’re removing the barrier and probably into you.”

Or Not Interested …

Short, coarse answers and asking no questions in return mean they’re not feeling it, Gopman says. The same goes for not making eye contact and looking around the room. That’s OK. Move on and keep talking to people. “They don’t know you yet as a person, so it’s really not personal,” she adds.

Ask For Their Number

You’re both vibing, so keep the conversation going at least five minutes or longer, asking questions and building a connection, whether you’re talking about travel, pets, music, etc. “[They] needs to feel enough of a conversation for a connection, then there’s a greater likelihood of [them] texting back the next day,” says Gopman.

“Don’t be a phone number bandit and make it all about the digits … The goal is a genuine connection and a date with someone awesome.”

“After talking, you have two options: say something like, ‘I don’t have a photo of my dog on my phone but I can text it to you tomorrow, what’s your number?’ Or option two: ‘I’ve got to run but it was really nice meeting you, let me grab your number and we can talk later.’”

Now you have them hooked and wanting more.

Warning: “Don’t be a phone number bandit and make it all about the digits,” Barrett warns. “The goal is a genuine connection and a date with someone awesome.”

Don’t Run Away

You got their number. Now linger. “Follow up with the conversation another minute or two then say, ‘OK, listen I’ve got to run but we’ll catch up again soon,’” Gopman says. “The most important thing is [they feel] comfortable and special.” Before the end of the night, or preferably after getting the phone number, send a text with your name and some description of who you are (i.e. “the cute guy at the bar with the striped shirt.”)

date couple coffee phone
Yiu Yu Hoi/Getty Images

Wait a Day to Call or Text

Don’t get caught up in the game of measuring how long you respond. For the first text or call, wait at least until the next evening. Then, rekindle your connection. Talk first and make sure they’re still responding and asking questions in return.

Ask Them Out

It’s time! Don’t say, “What are you doing Monday?” Instead, find out when they’re free. “Don’t get stuck to one night,” Gopman says. “First, find out [their] schedule and say, ‘Perfect, X night let’s grab a drink and go to this fun place/my favorite bar.’”

Remember to make it clear your interest is romantic.

Remember to make it clear your interest is romantic. Barrett suggests a text like: “Hey, we should [awesome thing together]. It would be cool to see you. Up for it?” He says the key phrase is “It would be cool to see you” because that vulnerability lets them know this is about the two of you connecting, rather than the activity.

Start with a date that doesn’t have a long time commitment. “Something where you can concentrate on the conversation, like a walk, coffee, or a drink,” Gopman adds. “Save your wallet and see if [their] worth it. A lot of girls don’t like a full dinner at first anyway, and drinks can last 30 minutes or all night. It’s a great test to see how you two get along.”

If It’s a No …

“Let them know that it’s totally OK,” Barrett says. “Respond with, ‘No problem. You’re so charming that I had to ask, but my heart will go on.’”

Setting Up the Date

Sit somewhere so it doesn’t feel like an interview. For first dates, Gopman recommends sharing a bar top and not being directly across from each other, that way you can start small touches as well. Here’s your guide on how to dress.

The second date should be an activity. Go bowling, to an arcade, ice skating, “something cute and fun that doesn’t rely only on conversation,” Gopman says. “The third date, go to dinner.”

No Dates?

Don’t lose your confidence. Congratulate yourself on getting out there and taking a risk. You’ll find the right person who enjoys your dad jokes and favorite dive bar.

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