14 Tips To Flirt Your Way Into Conversation With A Man


Learning to flirt
Too shy to make the first move? Don't be! Start with a spiffy opener and take it from there.

Often when coaching single female clients, the topic of talking to men comes up. In particular, talking to men they've never met before or men who seem interesting. Basically, they want to know how to flirt with strangers. 

I've noticed these women's answers tend to fall into two camps:


  • "I'm OK talking to him if the man starts the conversation."
  • "If the man starts by saying something embarrassing or awkward, I'm not OK with talking to him."

I tell these clients that there's a third thing to consider, which is: did you know that, in general, men are quite flattered when a woman talks to them first? Men are usually the ones who walk all the way from the other side of the bar to approach a group of women (we're always in groups) to ask one of the women to dance. And after that, the woman has to confer with all her friends about whether she should accept. Perhaps it's not surprising that men feel relieved to be approached!

But then the question comes up: How do you start a conversation with a man who is a complete stranger? You'd be surprised how easy it is to overthink this one. Here are a few simple ideas to try when you see a man close by who seems interesting.

Compliment him (on anything that's true):

  • Do you like something he's wearing? Say, "Nice shoes! Where'd you get them?"
  • At a conference or workshop, you notice him because he asked a great question. Seek him out on a break, tell him that his question was interesting, and ask what he thought of the answer he was given.
  • At the gas station, when he's getting gas at the pump next to you, tell him you like his car and ask why he bought that model. If it's racy looking, ask him how often he stays within the speed limit.
  • In an elevator, ask him to push the button for your floor. Then say something like, "You must add this talent to your resume — because you did such a great job — what other skills do you have?" Another good question: "If the president got in the elevator what would you ask him?"

Just say "hi":

  • I know this sounds too simple. But every man I've said "hi" to was quite flattered.
  • This just doesn't happen to men very often so they're usually surprised and caught off guard and happy to answer back.

Ask him a question about what's going on:

  • You're out country line dancing with a girlfriend. Ask him what dances he's familiar with. If you don't know one of the dances he mentions, ask if he'll teach you.
  • You're on the beach. Tell him if you had an empty bottle what message you'd put in it — and where you hope it would eventually land. Ask him what he'd put in a bottle and where he'd like his to land. Then ask him if he found a bottle on the beach what he'd like to discover inside.
  • You meet him at a party. Ask what route he took to get there. Why did he pick that way? This conversation can have lots of possibilities, such as (1) if there are two ways to get somewhere, do you have a favorite or do you alternate between the two or (2) what do you think about the gridlocked streets in that area or (3) do you really think government money should be spent on that particular road construction? This last one could turn into a heated debate, so be aware!
  • At a sporting event. Ask him which athlete in which sport he'd like to practice with and why. Another great question: if you could have two super powers as you play a sport which ones would they be? (Lots of men say flying so it's fun to ask them for two.)

Tell him something you know and ask his opinion:

  • In the grocery store you could say, "I like the Roma tomatoes because they have a better flavor for sauces. Which ones do you like?"
  • At a coffee shop you could say, "I've heard that even when you ask for decaf coffee there can be residues of caffeine in it." 

In closing… a couple more thoughts for you:

  • Always smile when you're talking to a man. This lets him know you're open to speaking with him and enjoy his company.
  • Here's a bonus question which is fun in any setting: "I've been thinking about the Nobel Prize lately. What do you think you should win the prize for? And why?" (Ladies, be prepared with your own answer to this question)!

Let me know if you use any of these and how they work. Ladies: send me lines you've used that worked. And men: tell me what lines would work for you!

And if you're feeling stuck, then let's talk. Click on the What's Holding Me Back From Love survey on my website.

Christine Baumgartner
Dating and Relationship Coach
YourTango Expert

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Christine Baumgartner

Dating Coach

I believe you want to love and be loved. And if the love you desire and deserve isn't currently in your life, then let's talk so you can turn the “work” of love into play by putting in place the right techniques for you to finally bring that love into your life.

I know (because it's how I met and married my husband) that once you become The Perfect Catch you'll definitely attract The Perfect Catch.

Christine Baumgartner

Dating and Relationship Expert

The Perfect Catch



Location: Laguna Niguel, CA
Credentials: Other
Specialties: Dating/Being Single Support, Life Transitions, Marriage
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