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40 Questions to Ask Your Crush to Subtly Flirt with Them

questions to ask your crush

Flirting with your crush is important when it comes to sparking up a new relationship. Make sure you’re doing it right by asking these questions.

When it comes to your crush, you always want to find a way to let them know you’re interested… without overkill. I’ve seen this so many times, and honestly, it’s never easy to watch. A lot of times, people think that flirting should be straight-forward so the “flirtee” gets the hint.

However, finding a connection with someone you’re interested in can be much easier when you do it in a subtle manner. By making a point to ask them questions and get to know them, you’re pointing out how much you like them, but you’re not flirting so much that they feel trapped.

Flirting should always be subtle and easy. Someone once told me that the best way to flirt with someone is to leave them wondering if you’re flirting. [Read: How to flirt with a guy without really flirting at all!]

Yes. It should be that simple. [Read: 12 essential flirting tips every guy needs to know]

Questions that will light the fire within your crush

Some of the best questions to ask your newly found crush are ones that help you get to know them and draw attention to their personal life. These 40 questions will plant the idea that you’re interested and help you find out more about them, their interests, and their personal tastes. [Read: 9 quick ways to know if your crush isn’t into you]

#1 Have you been working out?

#2 What are you looking for in a girl/guy?

#3 How can someone like you not have a boyfriend/girlfriend?

#4 How did you get so attractive?

#5 How are you so good at _______?

#6 What would be your ideal date?

#7 Why are you so funny? [Read: 40 unbelievably cute things you can say to your crush]

#8 What did you first think of me?

#9 What’s the most romantic date you’ve ever been on?

#10 Who’s your celebrity crush?

#11 Who do you think should make the first move? Guys or girls?

#12 Would you rather be considered sexy or smart?

#13 Are you looking to get a boyfriend/girlfriend anytime soon? [Read: 6 subtle questions you can ask your crush to know if they like you back]

#14 What’s the one thing that makes you the happiest?

#15 What do you wear to bed—if anything?

#16 Would you ever go to a nude beach?

#17 What would you do if I told you how attractive you are?

#18 What are your favorite pet names?

#19 What’s your biggest turn on when dating someone?

#20 How would you describe yourself in 3 words?

#21 Okay, now how would you describe me in 3 words?

#22 Are you a butt or a boob guy? Be honest. [Read: 36 racy, random questions for flirty guys and girls]

#23 What’s your favorite feature on a guy/girl?

#24 Do you find tattoos sexy?

#25 Have you ever been skinny dipping?

#26 *If answer to previous question is “no”* Would you ever go skinny dipping? 😉

#27 Are your parents as good-looking as you?

#28 What’s the most embarrassing thing that’s ever happened to you when you were with a significant other?

#29 Would you prefer to make out or cuddle? Or make out, then cuddle? 😉

#30 If you could have any job in the world, what would it be? [Read: 20 revealing questions to get to know someone a lot better]

#31 Do you prefer a pool or a hot tub?

#32 Have you ever had sex on the beach? No. I don’t mean the drink.

#33 What’s one thing you would lie about to your girlfriend/boyfriend?

#34 What’s the naughtiest thing you’ve ever said to someone?

#35 What was your very first date like?

#36 What makes you the most nervous? [Read: 50 questions to check if someone’s right for you]

#37 Would you rather be invisible or have x-ray vision? 😉

#38 If you could change one thing about your life right now, what would it be?

#39 What room—other than the bedroom—gets you going the most?

#40 How about we go out sometime?

[Read: The right way to talk to your crush and make them fall hard for you]

These forty questions are great to spark an initial conversation with your crush—or more. If you are nervous, shy, or unsure how to get a relationship off the ground, use these phrases to put you and your prospective amour at ease, while learning more about them.

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Bella Pope
Bella Pope
Bella is a lifestyle writer, cheese enthusiast (Wisconsin native over here) and fantasy adventure author-in-progress who enjoys all things love, dog, p...

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5 thoughts on “40 Questions to Ask Your Crush to Subtly Flirt with Them”

  1. Tim says:

    What are my favourite pet names is perhaps the question I like least. It’s something girls tend to ask me. For what reason, I don’t know, but it completely rubs me the wrong way. It’s not something I appreciate (having a pet name) and it’s not really something I’m all that into doing for others. Really, it’s just a huge sign of disrespect in my eyes and I’d much rather not have to cross that line, especially right in the beginning of a new relationship. Sorry, if that makes me boring, then so be it. It’s just not something I’m going to ever be into!

  2. ourasa says:

    I’m in a happy, healthy, open marriage and am allowed to date and see/sleep w women. two years ago I befriended this wonderful and beautiful older woman. She’s very flirty w me (and sometimes my hubby too) which got me very excited to build a friendship w her in hopes it could go “further,” because I am SOOO attracted to her. She is also married, and we feel like they aren’t totally straight, we have even spent the night at their house socially, but the only thing that happened was yet more innocent flirts. If they were swingers, wouldn’t they have made a move by now? Are they waiting for us to make a move? When her and I are alone she always hugs me a lot, is very affectionate, and makes flirty jokes. Then other times she acts very straight. I don’t want to burden her by being selfish and putting a strain on the friendship by telling her I have a crush. At same time, I am DYING to know if she is attracted to me too. It’s sexual torture to be in her presence. I’ve tried subtle ways to find out but still haven’t.

  3. Dating says:

    I can’t say I’ve ever been THAT oblivious, but at times I’m that shy guy. A lack of self confidence really plays a role in this ignorance on top of the fear of making a move. If a guy is on a big dry spell and/or has been down on himself lately, he’ll be nearly immovable in the flirting process. That move will seem nearly impossible even if a girl is on his lap. I’d even say experiences from growing up could be a factor. It really doesn’t matter how obvious the girl is or how bad he wants it, since the real wall here is self confidence. The best advice that I can give to a guy like this is to step out of your comfort zone, preferably with someone new as messing up means much less. Build up confidence one conversation at a time, you’ll find what works. Once you feel the charm and charisma pumping, you’ll feel like a new man. The moves start to come naturally, and the fear starts to fade. Most importantly, don’t let failures get to you.

  4. Penpal says:

    That’s called “preening” and not only girls do it. Us guys do it too! For guys, we tend to stand a little taller or puff our chests out slightly. Sometimes we smile with teeth a little more like a wolf does to assert dominance. Also, when having a conversation, make a quick note of the feet of the person you are talking to. If they are interested and engaged their feet will be pointed at you or crossed as not to intend to go anywhere anytime soon. If they are pointed elsewhere, you’re already in an uphill battle.

  5. runner says:

    Like anything else, conversation and social skills are skills, and they can be practiced. Start conversations with anyone, try to hold them for as long as socially acceptable. At the store, bank, school, customer service people on the phone, anywhere. I was blasted last weekend and walked up to this ghetto dude outside a Denny’s blasting shit tier rap in a blue tooth speaker. Instead of being pissed at his rudeness we talked speakers and joked around about shit for a bit as my group waited for a table. Guy was really nice past his facade of hood, and even tried to give me a blunt when I told him my buzz was fading Put yourself in situations that you’re not totally comfortable with, don’t let being made fun of or feeling out of place stop you. Anyone past high school that would make fun of you for doing something new is an asshole and the problem isn’t with you but then. Find groups that revolve around hobbies you have, or things you would like to try. Be friendly, be conscience or your facial expressions, your stance, your tone, and your speech speed. Focus on them, get them right and repetition repetition until its nature. For some people they just don’t over think it and have developed it over life and seem so damn natural at it. Some have to practice it, and there is no shame in that. There is shame in not trying and being bummed out about it.

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