Good Conversation Starters: 3 Sure-Fire Tips to Flirt Successfully and Break the Ice with Women or Men
Here’s practical advice for meeting women or men. You’re waiting for an elevator or you’re squeezin’ the Charmin at the market when you spot someone intriguing. You break the ice with a smile. Even a slight chin or eyebrow lift can get his or her attention. Next comes the fun (or scary) part: saying something. But what?
These three conversation tips guarantee that you’ll always know how to start a conversation. Better yet, you’ll always have something relevant and attention-getting to say. The point of using these tips is to create friendly rapport. You never know where conversation starters might lead. Just as an acorn grows into a mighty oak, small talk grows into real conversation. And beyond.
Tip #1: Compliment someone sincerely
Compliments pack a double whammy:
- First, everyone loves sincere compliments. They get people’s attention and create a receptive mood for good conversation.
- Second, when you’re looking for ways to pay a compliment, you’re looking for the good in—or on—someone else. That takes your focus off yourself and your rating on the Confidence-o-Meter and puts it where it belongs: on the person you want to talk to.
Obvious items to mention include clothing, accessories, and shoes. On a more personal level, consider haircuts, smiles, fitness, and body art.
For example,
- “Great shoes!”
- “Love your briefcase/purse/necklace/earrings/blouse color….”
- “What an unusual/striking/colorful/attractive/interesting/unique bracelet!”
Bonus tip:
If you’re tongue-tied on your feet, check your online thesaurus for adjectives. Make a list. To keep them at the top of your mind, review them daily or weekly.
Tip #2: Follow-up your compliment with a question.
Ask a question that calls for an explanation, not a short, pat, one-word answer. The meatier the question, the better. For example:
- Too pat: “Great shoes! Where did you get them?” will do when you can’t think of anything else to ask about them.
- Better: “Great running shoes. There are so many styles and brands. How do you decide which shoes to buy?”
- Too pat: “That’s a flattering color on you. Did you have your colors done?”
- Better: “That’s a flattering style on you. How did you learn to dress so well?” (A terrific follow-up to that is “What other talents do you have?”
- Too pat: “You look like a creative person. Are you an artist?”
- Better: “You look like a creative person. How do you express your artistic flair?”
- Too pat: “Love your ring/watch/shirt. Was it a gift?”
- Better: “Your ring is unusual. Does it have a story?” ["Does it have a story?" is one of my favorite follow-up questions because people love to share their stories.]
- Too pat: “You look fit. Do you work out?”
- Better: “You look fit. Tell me how you got that way.”
If you can’t think of a follow-up conversation question, that’s okay. Give yourself points for breaking the ice. Be a good coach and tell yourself “You’ll do better next time.”
Tip #3: Practice, practice, practice
Three ways to practice breaking the ice:
- Compliment one person, any person, every time you’re waiting in line to buy something. Tell yourself that you’re getting experience so that when that attractive someone comes along, you’ll be confident of your ability to break the ice. There’s nothing at stake, so go for it.
- Sit down at a mall or park. Think of a compliment and follow-up question for every person who walks by. If someone is close enough, say it out loud. Have fun!
- Get a magazine. Think of a compliment & question for each person in the pictures and ads. If you’re intimidated by attractive women — or men — focus on them.
Once you’ve broken the ice, keep the conversation going by asking more good questions.
Never be tongue-tied again. Get your free copy of “15 Sure-Fire Conversation Questions for Dates, Parties, and Hanging Out With Friends.”


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