For the Wealthy, Ambitious Man – 5 Unique Conversation Starters for Your Next Date

For the Wealthy, Ambitious Man – 5 Unique Conversation Starters for Your Next Date

You might be the most intelligent and brightest man in every room. You might work as hard as the elite athletes that everyone applauds. You might be at the top of your field. But, sometimes, this doesn’t make talking to a gorgeous, stunning woman any easier. Not in a natural, charming way, anyway. So if you want to hone your skills in dating models (which is perfectly possible, by the way, with an exclusive dating service like Lyons Elite), then it is certainly a good idea to equip yourself with several intriguing, unique, and definitely interesting conversation starters.

To that end, here is a curated list of 5 unique conversation starters you can use for that next model you date.

1. “Would you ever be willing to have a dangerous job – such as a lion trainer, a special agent, or a professional jewel thief?” This is a good conversation starter because it reveals something about the woman you are going out with. How bold is she – how much of a risk-taker is she? There are other variants of this question that you could also choose to use. For example, you could ask something like, “Would you ever be willing to do risky activities like go car racing, bungee jumping, or paragliding?” And, for a slightly flirty question, ask her if she’s ever gone skinny dipping – or if she would be willing to.

2. “What are the main 3 things you look for in a partner?” A deeply introspective question that will make her pause to reflect. Ideal if you’re aiming to engage in a deeper conversation. What’s more, her answer to this question can open the door to other questions, such as WHY she wants those 3 things in a partner.

3. “Have you ever crushed on someone of the same sex?” This is another interesting question that leads her to open up to you a bit more and builds a sense of rapport. And, in you would like to add a dash of humor to the conversation, you can always say something like, “Me? Oh, I’ve had the biggest man crush on Dwayne ‘The Rock’ Johnson!”

4. “Have you ever been in love with 2 people simultaneously?” A great conversation piece because she will invariably offer various tidbits on her thoughts on romantic love. And, since it reveals something about her past, it will make her feel a bit closer to you – she’ll feel more at ease in your presence.

5. “What’s the dumbest thing you’ve ever done?” This is a fun question that could very likely lead to smiles and giggles all around. Not only will her answer to this show you some interesting aspects of her personality, but there are many directions this conversation can go.

Of course, dating models will be a lot easier if you have a luxury matchmaker to coach you on dating and advanced social skills.

Lyons Elite is an Exclusive Matchmaking Service in Toronto Where the Successful Come to Find Their Perfect Match. If you have any questions, do not hesitate to contact us at

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