53 Questions to Ask Your Crush the Next Time You Talk

Even the most confident conversationalists know that talking to a crush can leave you tongue-tied. Not only do you have to come up with a bunch of insightful questions to ask in order to keep the interaction moving, but you also have to make a winning impression. Plus, as the conversation progresses and you learn more about your crush, you also have to do the mental analysis of whether you and this person are actually compatible.

While we can’t make that ultimate decision on your behalf, we can help you come up with questions to ask your crush to get to know them better. In learning about certain key areas of their life—namely, their daily lifestyle and interests, their relationship with family and friends, and their communication style—you’ll hopefully start to sense whether the two of you could work as a pair, says Jonathan Kirkland, head of marketing and brand for BLK, the largest dating and lifestyle app for Black singles.

“You have to be real with yourself as you continue to get to know your crush,” Kirkland says. “If you begin seeing red flags but are still smitten with your initial attraction to that person, you may run the risk of becoming ‘colorblind’ to these red flags. Pay attention to the person you see in front of you, not the person you think and/or hope that they will become.”

Make sense? Great! Remember, when you deploy these, it’s normal for your convo to get a little awkward—a lull in conversation isn’t necessarily a bad sign. “When you think about it, anything in life that’s new starts off a bit uncomfortably,” Kirkland says. “Just work through it, keep going, and enjoy those moments of awkward silence.”

Questions About Your Crush’s Daily Lifestyle and Interests

“I don’t mean bathing, getting dressed, or bathroom behavior (that would be extremely weird),” Kirkland says. “I’m referring to common activities people do daily: watching TV; listening to music; and other lifestyle habits. Examples: What shows did you binge watch during quarantine? What’s the best ’90s R&B group? On a Sunday, would you rather hike Runyon Canyon, or get lit at a boozy brunch?”

Try these:

Questions About Your Crush’s Relationships With Friends and Family

“If he/she/they seem(s) to frequently be at odds with friends and family, there’s a good chance that the real problem here is your crush,” Kirkland points out. “Some good questions to ask to get this intel without seeming too intrusive can be: When’s the last time you talked to your parents or siblings? Now that people are getting vaccinated, do you plan on visiting your family, or are you planning any vacations with friends? What was the last group vacation you took with pre-Covid, and how was that?”

Try these:

Questions About Your Crush’s Communication Style

This is simultaneously one of the most overlooked, yet most important pieces of information to gather when you’re getting to know someone, according to Kirkland. “Some people solely text; others love to call and chat. Let’s not forget about the bold ones that will just FaceTime you with no prep time given—and then there are those who can have entire conversations using ONLY gifs and emojis,” he says. “A simple question here is basically, ‘Are you a phone or a text person?’ Then, as you speak more, you’ll develop your own little groove of communication.”

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