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First Date Conversation Tips for Older Singles by Jacqui Baker, Dating Mentor & Matchmaker

Butterflies in your stomach? First-date jitters are normal, especially when you're back on the dating scene again as an older single. But fret no more!

Hello, I'm Jacqui Baker. I'm here to support and guide fabulous older singles like you in finding connections that matter.

In this blog, I'll share my top conversation tips to help you sail through your first date with confidence, make a sincere connection, and leave a lasting positive impression.

Feeling stuck on small talk? 

Pre-date prep: Let's do away with the pressure of overly complicated first dates. Keep it simple and casual, focusing on conversation.

Light & positive topics: Let's explore some conversation starters that keep the mood light and upbeat:

  • Hobbies: We all have passions! Discuss what you enjoy these days, whether it's gardening, volunteering, or learning a new language. Ask open-ended questions like, "What do you do for fun outside of work?" or "Since retiring have you recently picked up any new hobbies?"

  • Travel: Share your travel experiences or dream destinations. This can be a foundation for exciting stories and future travel plans together! It doesnt have to be Acapulco or Zimbabwe - it could be a visit to Edinburgh or a hike in Snowdonia.

  • Careers (working/retired):  Work and career aspirations offer an insight to your date's lifestyle and goals. Chatting about these helps you understand how they spend their days and what excites them.

For retirees, explore how they're enjoying their free time, travel dreams, or new skills they'd like to learn.

Active listening: Remember, Jacqui's golden rule: listen actively! Aim for 70% listening and 30% talking.

Additional Tips:

  • Humour: A touch of lighthearted humour can break the ice and build rapport. Let your personality shine through!

  • Be present: Put away your phone and focus fully on your date. Make eye contact and show genuine interest.

  • End on a positive note: Thank your date for their time and let them know you enjoyed getting to know them.


The key takeaways from this blog;

  • Do a little date prep - think about some topics to chat about and a couple of little interesting things about yourself that you would like to add in to the conversation.

  • Keep the conversation light and positive.

  • Listen actively, be interested in what your date is saying.

  • Use a little humour.

  • End on a positive note.

If you're feeling a bit unsure, I'd love to help. Reach out to me, Jacqui Baker, for personalised coaching. Together, we can create a first-date strategy that suits you perfectly. You can find me at

Jacqui Baker


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