7 Conversation Starters to Use with a Guy Youre Crushing on ...

By Lindsey • Feb 26, 2014

Striking up the courage to talk to a guy you’re crushing on can be nerve-wracking, and searching for the perfect conversation starters can be equally as frightening. However, there are extreme upsides to taking the lead in flirting with a guy. By starting the conversation, you’re showing initiative and proving your confidence. So go ahead, take a look at this list of conversation starters and try putting some of them to the test!

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1. Proudest Moment

A friend of mine suggested that one of the most interesting conversation starters is to ask a guy what his proudest moment is. This can open up the doorway to several new topics, and will definitely teach you a lot about who you’re talking to.

2. Funniest Moment

On the flip side, by talking about a funny moment, you get to see what the guy’s sense of humor is like. In turn, sharing your funniest moment too will help you loosen up and have a good laugh with your crush.

3. Family Life

Often times, the way to a guy’s heart is through his family. A man’s family dynamic can tell a lot about who he is and how he got where he is today. Not to mention, taking interest in his personal life shows your caring and considerate side.

4. Ideal Job

Talking about what you do for a living is all well and good, but this can get dry pretty quickly. After a while, it can seem as though you’re in a business meeting instead of flirting. Ask your crush what his absolute ideal job would be and learn about his dreams and goals. If he says that his current job is his ideal job, bonus points for him.

If you're looking to engage your partner in intriguing conversations, why not try some hypothetical questions for couples? These fun queries will not only keep the conversation lively but also stimulate deep thoughts and potentially reveal insights about each other's personality and thought processes.

5. First Concert

I personally love asking this question because everyone seems to have such an interesting first concert that they attended (for me: Cheap Trick). Sometimes this answer can be really funny too, like an O-Town concert when he was 12 (O-Town, anyone?). This can also lead to topics such as favorite music or favorite song. The possibilities are endless!

6. Pet Peeves

This topic could strike a sour chord, but at least this way you’ll learn what things he really doesn’t like and what to avoid! Some people can have really silly pet peeves too, so this topic can help lighten the mood as well. However, when you’re sharing, be careful not to go too far in to detail about how much you hated the majority of the people you went to college with, as this can scare him off pretty quickly.

7. Your Life Movie

Ask your crush which actor would play him in the movie about his life. This one can be hard to think of, but also pretty hysterical. It’s always interesting to see who they would pick! There’s a lot that can be said about a guy who chooses Adam Sandler versus a guy who chooses Tom Hanks.

Ladies, don’t be afraid to take the wheel when it comes to talking to guys. It’s a total turn-on for them to see a girl who isn’t afraid to approach them first. Worst case scenario, the guy isn’t interested. These things happen, so just move on to the next one. I’d love to hear some of your ideas for great conversation starters. Please share in the comments!

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Where Thoughts and Opinions Converge

  • Sweetheart31

    2014-03-22T12:47:22.306Z

    That's the first time I talked I ben
  • Audrey

    2014-02-27T07:40:31.886Z

    Talk About cross-fit :)
  • Kymie

    2014-02-27T07:10:55.105Z

    What about a sport his interested in, that's often really good.
  • Sweetheart31

    2014-03-22T12:47:10.687Z

    Well what worked for me I said hi to Ben the I asked him how is day was going ? He told me good and he asks me I said its good
  • Yeela

    2014-11-21T14:11:00.233Z

    I actually wrote to him yesterday and he answered me with a 😘 .. but now when I'm trying to build up a conversation it's like I'm just asking questions and he answers like very distanced ... What should I do ? Keep taking to him ? We have been studying together for the past 9 years and yesterday was the first time I have ever talked to him...
  • Duckyfangirll

    2014-03-02T07:39:47.713Z

    My fanboy friend and I used to talk about fandoms and things we liked; good times Or you could get to know, you know, the deep stuff. Like "what's your favorite color?" -Catching Fire, Peeta
  • JustHayHay44

    2015-01-30T00:01:43.719Z

    In my career development class we are working on a project about what we want to do in the future, and i was thinking about asking him that today! Maybe I'll try it tomorrow!
  • Emily

    2014-02-27T07:06:32.161Z

    Very helpful :)
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