How To Ask Someone Out: 8 Tips From Dating Experts

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.

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."

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." 

"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."

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.

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.

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.