Whether you wanna be bold or subtle, you’ll be using at least one of these in the future, we promise.
You’re talking to someone that you’re into, it’s going well, you really dig the guy, but you wanna to amp up the flirtiness factor a bit to see if he’s feeling the same way. Whether you’re on a date, or just at that first meet-cute moment, bridging the tone from “this could be something” to “yup, this is 100% a Flirty Conversation™️ now” doesn’t have to be hard! The good news, is you can totally steer a convo into flirtier territory just by asking the right questions.
We polled some relationship experts and put together this handy guide of the 10 flirtiest questions to ask a guy. Feel free to use one to lead the discussion and go from there, or hell, memorize them all to have in your back pocket just in case!
1. “HOW WOULD YOU IMAGINE OUR FIRST DATE?”
This question, courtesy of Beverley Andre, LMFT, owner of BeHeart Counseling Services and Your Favorite MFT, is great if you’re not quite on a date yet, but ~vibes~ are being exchanged. Not only is it like a “Hey, I’m interested, are you?” check, but you also get the bonus of easily segueing to making those said imagined date plans a reality.
2. “WHAT DOES IT TAKE TO GET A SECOND DATE WITH YOU?”
This one, also suggested by Andre, is a good option if you’re already on a date. It does the same thing as the above, letting the guy know you’re into him, and puts the onus on him to volley any flirtation or second date ideas back over to you.
3. “WHAT DID YOU NOTICE FIRST ABOUT ME?”
Yue Xu, co-host of the Dateable Podcast, considers this to be one of the flirtiest questions you can ask a guy. Not only does it more than likely set you up for a compliment (words of affirmation stans: I see you, I am you), it’s also a good way to find out what they consider important. Was it your looks, your personality, etc? Plus, the natural progression of asking this question means you’ll also get to share the first thing you noticed about him.
4. “OTHER THAN THE OBVIOUS, WHERE DO YOU LIKE TO BE TOUCHED THE MOST?”
Xu recommends this one, and it’s easy to see why. This question is capital F-flirty. Not only is it bringing any conversational chemistry to focus on becoming physical chemistry, it’s also great info to know for a later time, should you want to go ahead and graze his inner arm or ears, or whatever body part he answers with.
5. “IF YOU HAD TO USE A MOVIE TITLE TO DESCRIBE YOUR KISSING STYLE, WHAT WOULD IT BE?”
The great thing about this question by Xu, is there’s room to answer with humor and be flirty at the same time. Everyone likes talking about themselves, and odds are pretty good that this isn’t a line he’s heard before.
6. “WHAT’S YOUR STANCE ON A WOMAN MAKING THE FIRST MOVE?”
Samantha Moss, editor and content ambassador at Romantific, says this question is great for two reasons. On the surface, it’s a subtle way of communicating that you’re willing to make the first move or that you want to make the first move, and it can also leave the guy wondering about what exactly that first move may be.
7. “HOW ARE YOU STILL SINGLE?”
Moss says this is the perfect question to not only compliment a guy, but also send a hint. Just by asking the question, you’re sending a signal that you’re into him.
8. “WHAT ARE YOU KIND OF OBSESSED WITH THESE DAYS?”
Channa Bromley of Relationship Hero, suggests this one as it allows the guy to talk about his passions. “People are drawn to others who live passionate lives,” she explains. Passion and enthusiasm about anything — whether it’s a hobby, a book they can’t put down, a show they’re binging, is sexy. This question also allows you to talk about your own passions as well. Not only do you get to learn more about them, you get to showcase yourself as well.
9. “SO, HOW WOULD SOMEONE USUALLY LET YOU KNOW SHE LIKES YOU?”
This one is bold but it’s also ~smooth~ because after they tell you, you can just go ahead and do that, explains May Hui Bugenhagen, of Matchmaker May.
10. “WOULD YOU LIKE TO HANG OUT AT MY PLACE?”
If you’re already on a date, this question by Andre, is a great segue to move things along. You can always tweak it to be like, “Do you wanna come over for some coffee,” or inviting them back up for another drink, but the message is the same. It’s about to get on!