20 Flirty Questions To Ask A Guy

Play the game 20 Questions to ask a guy and take turns asking each other fun, interesting questions and make the getting to know you process much more easier. Been dating a while? Come up with creative questions that you could ask him and get even closer…don’t let those in the ‘honeymoon’ stage have all the fun!

These are geared towards those guys that not only have potential, but those you have your eyes set on.  You don’t want to be too over the top or come across too forward, but you can let him know you’re interested and take it from there…

• “I Haven’t Seen You Before…Are You New Here?” This is such a simple opening line…not only are you starting up a conversation with him but you’re pretty much making him have to respond. This works only if it’s a place that you’re used to, or have at least gone several times prior…it’ll be pretty strange if he asks you as well how often you go there and you respond with ‘it’s my first time’ or ‘once or twice’…use this one wisely.
• “Oh, what kind of drink is that?” If you see him holding a bottle of soda, beer or anything with an obvious label, then avoid this question! If you’re at a party or at the bar and you see the cutie you have your eyes set on drinking a glass of something, lean in and ask…seem interested (in the drink) and put a little cuteness in it….”Oh, that looks good…what kind of drink is that?”.  Maybe if you’re lucky, he’ll buy you one!

• “Are You Single?” Don’t ruin the vibe by asking this right off the bat because frankly, he could be just a friendly guy that is having a conversation.  You really would need to have a better feel for him by observing his body language, what he’s saying and if you’re getting the vibe…if all things are a go, put a cute smirk on your face and ask him ‘Are you single?’

• “We should hangout sometime…wanna text me your number?” I’ve used the ‘We should hangout sometime’ line many times in my dating game and I swear it works awesomely! Don’t just randomly go up to a stranger and ask for them to text you. Once you started a conversation with your guy and you guys have been hitting it off, you’re getting the vibe he’s into you, so throw this line in before ending the conversation for the evening.

This is the guy that you’ve been seeing pretty recently but it’s not your first time meeting. You guys are enjoying each other’s company and getting to learn about each other so this is a perfect time to throw a few cute questions in the mix.

• “What do you usually look for in a girl?” This is such a great question that I, myself and many friends have used dozens of times in our lives and it not only gets you the valuable information that you need (Ok, ok…maybe not need, but definitely want!) as well as give him that more than subtle hint that you want to be that kind of girl he’s looking for.

• “Have you been working out?” I put this as something to say when you are not only starting to see someone but also even if you have been dating for quite some time.  This would come across pretty awkward for someone you have just met.  When asking, make sure you say this in a complimenting tone so he knows exactly what you’re implying. ‘Have you been working out? You look great!”. Maybe he’ll give you a sneak peek of those muscles (wink wink!)

• “Wanna come keep me company?” Whether it’s hanging at your place with Netflix and snacks or for him to meet you at a party that you’re attending, this simple question shows him not only are you thinking about him, but that you want to see him.  Guys like feeling wanted and this is a perfect way to see your hunny and have him feeling good too! Just don’t become THAT friend that can’t hang out with her best friends without her man in tow…that really ruins things not only with your best friends but with your man as well.

This is the guy you’ve been dating a while, your sweetie, your bae and the guy you can’t stop thinking about.  When you’ve been seeing each other for some time the comfort level feels great and it feels like you guys could talk about anything.  This is the time where the braver questions/comments come in.  Just remember, don’t try to impress, be yourself.

• “I wish you were lying next to me…can you send me your smile?” This can be such a cute question when you and your babe are laying in your own beds, texting one another and missing each other.  What better way than to imagine them lying along side of you than with a photo of their adorable smile lying in their bed while you’re in yours.
• “Do you want to have a little more fun texting?” Ok, so there has to be some clarification with this one…It doesn’t have to mean sexting, it can also be a great opener to start playing 20 Questions. IF you are taking it to the next level and incorporating sexting, make sure you do it with great caution. Just remember, any inappropriate photos if under the age of 18 are illegal so keep that in mind (even if it is to your boyfriend). If you take any ‘suggestive’ photos make sure you avoid your face in the pics since guys aren’t the greatest at keeping it to themselves as much as they would promise you and if you break up, others won’t be able to tell it’s you. You can totally be sexy without giving up all the ‘goods’ either.
• “What would you do if I were with you now?”  This question could go super cute with an adorable “cuddle you” or “kiss you” answer but he could also do a 180 and may get a tad naughty with his response so make sure you are prepared. If you want to ask him but are hoping for a cute answer, let him know what you would do if he was with you that moment…”What would you do if I were with you now? I know I’d want you snuggling with me listening to music if you were here.”.

1. Make sure you have a relaxed smile…don’t force it
2. Body language is everything…gently touch his arm every so often while to talk to him
3. If you text, make sure you add a cute emoji so he sees your mood
4. Simply be your amazing self! You’re awesome, you know it!

These questions to ask a boy are a great way to let him know that you are interested and will get him thinking more about you.  You want to come off as cute and flirty but not pushy or ‘easy’  so make sure you ask these at the appropriate times and avoid asking him to send you a shirtless pic the first time you exchange numbers, or ask him what attracted him to you the first time you met if you just began a conversation.  Relax, be yourself and remember guys like confidence and happy girls are always the prettiest!