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. 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.) 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.” Things you can say instead: 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. “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.” 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.