3 Strategies for Indirectly Asking Someone Out

How to ask someone out with less awkwardness and embarrassment.

Posted March 5, 2026 | Reviewed by Gary Drevitch

As I wrote previously , dating and relationship conversations can be awkward and embarrassing. Those feelings arise because of an inherent conflict. On one hand, we are motivated to ask for what we want from a romantic partner. On the other hand, we don’t want to embarrass ourselves or make things awkward with them in the process.

To solve this dilemma, Kunkel, Wilson, Olufowote, and Robson (2003) studied how people initiated, intensified, and ended romantic relationships . In doing so, they identified the concerns that made people hesitate or give up on their efforts ( face threats ), as well as the strategies they used to persist and get what they wanted ( face-saving strategies ). In this post, we’ll explore the concerns that might hold you back from initiating a relationship—and the indirect strategies you can use to ask someone out with less risk and awkwardness instead.

Concerns When Asking Someone Out

To start, we need to know what concerns specifically hold us back from initiating a romantic relationship. What exactly is so anxiety -provoking about asking someone out? Kunkel and associates (2003) identified six main concerns that individuals worry about before initiating a relationship:

Exploring further, Kunkel and team (2003) found that individuals asking someone out are “highly concerned about whether they appear physically attractive to the other and also perceive moderate risk of looking too forward when pursuing this goal." In fact, some participants found these concerns so worrying that they decided to avoid asking altogether. This was particularly true for those who were worried about being overbearing, losing the current friendship, looking overly dependent, or giving up other possible relationships.

As a result of those concerns, only 61% of participants surveyed said that they would ask someone out. Furthermore, if that person initially refused the request, only 12% said they would try again at some other time. Rather than avoiding or quitting, however, others chose a less risky and anxiety-provoking option: discussing things indirectly.

Asking Someone Out Indirectly

Additional results from Kunkel and associates (2003) noted that some participants shared strategies to ask a partner out indirectly. Those indirect discussions were categorized on three levels, which fell between avoiding the conversation entirely and directly asking for a date without any prior conversation. Specifically, indirect initiating conversations were either (1) very indirect with only mild hints about going out, (2) somewhat indirect with strong hints about dating, or (3) somewhat direct with preliminary conversation leading to a direct request for a date. Furthermore, each approach had a unique strategy, as discussed below:

Participants with a very indirect strategy tended to ask general social questions and inquire about their potential dating partner. Usually, they introduced themselves (“Hi. My name is…” ), made a statement (“I always get the coffee here…” ), and asked a general question ( “What are you reading there?” ). This approach can be a good way to get a potential partner’s attention and create initial attraction . As I share in my book Attraction Psychology (2022), alternating between statements and questions helps break the ice and initiate conversation too. If your potential partner is responsive but hesitant, however, you may need to be more direct and do more talking to build a deeper connection.

Therefore, participants with a somewhat indirect strategy proceeded by inquiring about their potential partner’s interests and suggested activities to do together. This followed the pattern of asking about an interest ( “Hey, do you like ice cream?” ) and then, if they said yes, suggesting a shared activity ( “I know a great ice cream place where we could go sometime...” ). This strategy works particularly well after you have broken the ice and started a conversation—or when you already know the potential partner. It also aligns with other persuasive requests I have shared for indirectly asking for a date . Again, this step helps you test whether someone is interested, without having to face possible rejection directly. Sometimes, however, they still do not take the hint. So, an even more direct conversation might be required.

Thus, participants with a somewhat direct strategy progressed by having some conversation with the potential partner first (i.e. combining the first two approaches above) and then following up with a more specific date request. Kunkel and associates (2003) share that such a request was usually about a definite event, at a particular time, with a direct invitation to the potential partner (e.g. “Are you free this Saturday, because my friend is having a party, and I was just seeing if you wanted to go?” ). As I discuss in my book, these date requests can be made more persuasive as well (Nicholson, 2022). For example, sometimes asking for a small request first, like borrowing a pencil or asking for a napkin, can make someone more likely to say yes to your date request. Also, you can use the SPICE approach and make the request simple (don’t oversell it), aligned with their perceived self-interest (why should they want to go?), incongruent (get their attention ), confident (focus on them), and empathetic (connect with their feelings).

Put together, these three strategies provide a potential method for asking someone out indirectly. This approach also builds comfort and connection between you and a partner, if you end up needing to ask for what you want directly too. So, either way, it gives you the best chance of initiating the relationship you desire, while minimizing the concerns that could hold you back!

Nicholson, J. S. (2022). Attraction Psychology: Solutions for Successful Dating and Relationships . Amazon.com.

Kunkel, A. D., Wilson, S. R., Olufowote, J., & Robson, S. (2003). Identity implications of influence goals: Initiating, intensifying, and ending romantic relationships. Western Journal of Communication (includes Communication Reports) , 67 (4), 382-412. doi.org/10.1080/10570310309374780

Share this post Facebook Bluesky Linkedin Email

There was a problem adding your email address. Please try again.

By submitting your information you agree to the Psychology Today Terms & Conditions and Privacy Policy

Jeremy Nicholson, M.S.W., Ph.D. , is a doctor of social and personality psychology, with a focus on influence, persuasion, and dating.

Get the help you need from a therapist near you–a FREE service from Psychology Today.

This article is part of the Bringwise Psychology Journal — daily insights on human behavior, mental health, and personal growth.