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How To Ask Someone Out: 8 Tips From Dating Experts

Acamea Deadwiler, M.S.
August 29, 2021
Acamea Deadwiler, M.S.
By Acamea Deadwiler, M.S.
mbg Contributor
Acamea Deadwiler, M.S., is a freelancer writer and the author of 'Single That.' She has a bachelor's degree in public affairs from Indiana University Northwest and a master's degree in communications from Valparaiso University.

It's understandable that you may be apprehensive about asking someone out on a date. Nobody likes rejection, especially not in matters of the heart. It can be embarrassing or make once comfortable interactions seem weird. Then there's the pressure of trying to find the right words and the best time to make your move.

But if you never ask the question, you'll never know the answer. Instead of living with the "what if," use this expert advice to increase the chances of a successful date invite—and to be able to gracefully handle the occasional "no" when it comes.

Deciding when to take the next step. 

If you can't stop thinking about a person even after you've parted ways, it may be a sign that your interest in them is more than friendly. For instance, maybe you can't get out of your mind your friend's sister who you just met at a group outing, or you find yourself wishing you could spend more than just the five minutes talking to your barista at the register of your favorite coffee shop.

In deciding whether to take things to the next level, dating coach Kevin Carr says there are cues you can look for. "When you attempt to engage in conversation, does the person you're interested in match your energy, or do they reply with one-word answers to keep the conversation short and simple? You want to look for reciprocity here. If the interest you're showing isn't reflected back in your direction, you may want to take that as a sign to not try to advance the relationship." 

To pick up on these cues, clinical psychologist Jaime Zuckerman, PsyD, suggests starting with casual conversation. Don't "cold call" the request. Chat about the weather or a good movie you just watched. Once you've established mutual comfort, branch out into other topics to help you deepen the connection and open up to each other.

The good thing about developing romantic feelings for someone with whom you're already familiar is that you have a head start on building a rapport. Use that common ground as a foundation for nurturing the relationship, she suggests. "Being familiar with them usually means you already have some background information. Expand on this in conversation. For example, if it's someone at your gym, it would be an easy conversation starter to discuss something or ask a question that's health and fitness related."

Regardless of the scenario, these conversations will help you gauge the other person's interest (and your own!) before asking someone out. (Here are some signs of attraction if you're still unsure.)

How to ask someone out on a date:


Be assertive, not aggressive.

Confidence is attractive. Brashness is not. "It's important to be observant here and not too pushy," Carr says. "Remember to listen and let the conversation progress naturally." 

Zuckerman adds that you should "Preface the ask with an understanding of the circumstances. Acknowledge the potential weirdness of the situation. Give them space if they need to think it over to weigh the potential pros and cons."


Avoid the "D" word if uncertain.

"I actually tell my clients not to use the word 'date' immediately," says dating coach Rachel Freidus, LMFT. "That way, if the person is taken (or uninterested), they can convey that and feel less awkward."

Things you can say instead:

  • Can we grab coffee?
  • I enjoy our talks and would like to learn more about you.
  • Want to grab lunch sometime soon?
  • We should continue this conversation later.

"This language sounds more relaxed and ambiguous," Freidus continues. If they accept the invitation, you can use that time in a casual setting to learn their relationship status and whether they're open to dating you. At worst, it will be a friendly outing with someone whose company you enjoy.


Do it in private.

If you ask someone out in front of a group of people or even just a mutual friend, they could feel put on the spot and pushed to say yes. This environment may also make things a bit uncomfortable for you if they decline. Zuckerman recommends asking the person out in private. Pull them to the side if necessary.


Offer an easy out. 

If the person doesn't want to date you, make it easy for them to be honest about this. You don't want to go out with someone who doesn't really want to be there anyway. Zuckerman says a simple way to let them off the hook is to include in the conversation that you'd understand any hesitation or lack of interest on their part.


Be straightforward.

Once you know the person is single and it seems there's a shared attraction, Freidus believes you should make it clear that you'd like to take them on a date. Ask them out to dinner or for drinks. After you've established a connection, don't beat around the bush too long. Make your intentions known to ensure you're on the same page.

In person vs. text.

How to ask someone out via text, or whether you should or not, is "situation-specific," according to Zuckerman. She says it depends on the environment and the level of discretion necessary. Texting could be a viable option if that's the most tactful, private method of contact available. Or if that's the main way the two of you communicate.

Keep in mind, though, that assessing tone can be difficult via text. Messages are easily misconstrued. So, type exactly what you mean. Don't assume the other person will get your sense of humor or read between the lines of a text. This goes for online dating and social media DMs as well.

What to do when they're not interested.

Sometimes you can take every precaution and still misread the situation. You may think the other person is romantically interested in you when they're just being nice. Or they may really like you, but only as a friend. Whatever the reason, once you take the next step and ask them out on a date, there's always a possibility they'll decline the invitation.

"If you don't think you would be able to handle a 'no,' or that you, personally, would feel too awkward if rejected, it may not be a good idea to ask them out to begin with," Zuckerman advises. "Respect their decision. It very well may not be personal but rather a function of the circumstance itself." 

You can't allow the person's disinterest to negatively affect interactions or an environment the two of you may share. Keep it cool. Keep it moving.

As Carr points out, "No one likes being rejected. But it happens. It's important not to take it personally and to accept it with grace. Everyone won't be interested in you. You don't need them to be. All it takes is one precise connection to change your life."

The bottom line.

There's enough innate pressure in deciding how to ask a person out, whether that's someone close to you or a complete stranger. Don't add more stress to the situation. Build a relationship with the person and allow it to naturally progress. Then, detach from the outcome.

Letting someone know you have feelings for them requires a level of vulnerability. Be proud of yourself for taking the risk and putting yourself out there, no matter the result.

Acamea Deadwiler, M.S. author page.
Acamea Deadwiler, M.S.

Acamea Deadwiler, M.S., is a freelancer writer, speaker, and the critically acclaimed author of Single That: Dispelling the Top 10 Myths of the Single Woman. She has a bachelor's degree in public and environmental affairs from Indiana University Northwest and a master's degree in marketing and communications from Valparaiso University. She's a former Top 100 Contributor on Yahoo! with more than one million page views, and her work has been featured at New York Post, Blavity, FOX, and elsewhere.