Where Cars Meet Culture
Jan 13, 2025
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Dating: 10 Conversation Starters

5 years ago
1 min read

by Michael Satterfield

Sometimes just having an idea of where to start is all you need to get a good conversation going, guys don’t try those cheesy pick-up lines, just ask a relevant question about her life, work, or interests and you can get the ball rolling. If you are going to try to start a conversation, be sure you pick a subject you at least know a little about, so you can keep the conversation flowing.

Here are a few suggested topics, these are ideas, so make sure you make them your own and that they are relevant to your situation. Don’t just blurt “What’s your favorite holiday?” at her if there is nothing to prompt the conversation. Make sure you are using the right prompt for the right situation.

1. Where would you like to travel to?
This question will tell you a lot about a woman, her taste, and if you have anything in common. If your ideal trip is camping in Moab and hers is Five Star Hotels in Paris you may not be a good fit.

2. What is a skill you would like to master?
What makes her tick, what is she passionate, and if she is passionate about it, what is keeping her from chasing that dream.

3. Do you have any pets, or what pets did you have growing up?
People love talking about the animals in their lives.

4. What’s your favorite holiday?
A fun conversation starter that lets you talk about holiday memories. Holiday stories can tell you alot about a person and what they value.

5. What do you do to relax after?
This is a great conversation starter and will give you more insights into what she likes to do.

6. What is the best thing that happened to you this week?
This is a great way to start a positive conversation.

7. If you could live in any city, what city would you choose?
This question will give you a chance to find out what she really values, and gives you insights into if you might be compatible.

8. What was your favorite movie when you were a kid?
Movies we loved growing up bring up fond memories and gives you something light and fun to talk about.

9. What’s the worst job you have ever had?
People love to talk about jobs they hated and everyone has one they didn’t like so you can establish some common ground.

10. Where did you go on your last vacation?
People love sharing their vacation stories.

Michael Satterfield

Michael Satterfield is the founder of The Gentleman Racer, a leading automotive lifestyle site blending cars, travel, and culture. Known for its compelling storytelling and unique perspective, the site has become a go-to destination for car enthusiasts and style aficionados.

A Texan with a passion for classic cars and motorsports, Michael is also a hands-on restorer, currently working on a 1960s SCCA-spec Formula Super Vee and other project cars. As the head of the Satterfield Group, he consults on branding and marketing for top automotive and lifestyle brands, bringing his deep industry knowledge to every project.

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