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14 Tips For Flirting Your Way Into A Conversation With Any Man

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how to flirt with a guy
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Too shy to make the first move?

When coaching single female clients, the topic of how to flirt with a guy always comes up. In particular, they worry about talking to men they've never met before or men who seem interesting.

Basically, they want to know how to flirt with strangers. 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."

RELATED: 3 Conversations Starters To Help You Slide Into DMs And Make The Best First Impression


I tell these clients that there's a third thing to consider, which is that men are quite flattered when a woman talks to them first and whips out good conversation starters.

Men are usually the ones who make the long vulnerable walk 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 then confers with all her friends as to whether she should accept. Perhaps it's not surprising that men feel relieved when you approach them.

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. So, to help you out, here are 14 simple conversation starters to use with a man close by who seems interesting: 

Compliment him (on anything that's true):

1. Do you like something he's wearing? Say, "Nice shoes! Where'd you get them?"

2. If you're at a conference or workshop and you notice him because he asked/answered a great question, seek him out on a break, tell him that his comment was interesting, and ask what he thought of the other comments he was given in response.

3. 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.

4. 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" (and make eye contact):

5. I know this sounds too simple. But every man I've said "hi" to was quite flattered.

6. This just doesn't happen to men very often, so they're usually surprised and caught off guard and happy to answer back.


RELATED: How To Have MEANINGFUL Date Conversations (& Avoid The Awkwardness)


Ask him a question about what's going on:

7. You're out country line dancing with a girlfriend. Ask him which dances he prefers. If you don't know one of the dances he mentions, ask if he'll teach you.

8. You're on the beach, so ask him, "If you had an empty bottle what message you'd put in it — and where you hope it would eventually land?" Then ask him if he found a bottle on the beach what he'd like to discover inside.

9. If you meet him at a party, ask what route he took to get there. Why did he pick that way? This conversation starter 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) "Did you come that way from work? What do you do for a living?" or (3) "Do you really think the government should spend money on that particular road construction?" This last one could turn into a heated debate, so be aware!

10. 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 superpowers 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:

11. 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?"

12. 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." 

Try something more modest:

13. Always smile when you're talking to a man you're interested in. This lets him know you're open to speaking with him and enjoy his company.

14. 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.)


RELATED: 8 First Date Conversation Mistakes That Scare Him Off


Christine Baumgartner is a Dating and Relationship Coach. If you're feeling stuck, check out the What's Holding Me Back From Love survey on her website.

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