The First Date: How To Get The Conversation Going - 8 Tips

The First Date: How To Get The Conversation Going - 8 Tips

0 | 4113 views

Meeting a new potential partner on a first date can leave even the most talkative people tongue-tied and quiet. Instead of stumbling over awkward conversations and even more uneasy silences, use one of our almost fail-proof 8 tips on how to get the conversation started and keep it going when your first date jitters are looming. 



1. Focus on the Future


Dating over 50 has some fantastic perks. Even though you just met, a first date discussion about the future means that likely you both have some ideas on what you want the rest of your life to look like – and what you don’t want it to be, too. Sharing future hopes, dreams, or aspirations can be freeing and informative, since hearing what someone’s expectations for their potential life can help you decide if your evening will end up with a new friend or potentially something more. 



2. Ask For Advice


Without being philosophical, inquire about a hobby, interest, or something you or your match might do. Even if you don’t learn something new, you will likely spark a dialog about a topic that can be steered towards each other’s interests or abilities, extending the conversation possibilities. 



3. Share a Favorite Memory


Did you recently go on an interesting trip, visit with family, or have a one-of-a-kind experience? Use that as a springboard for first date banter. One caveat: since everyone brings a certain amount of personal relationship baggage to dating later in life, try to avoid bringing up relationship memories and leave those deeper conversations for future meetups.



4. Ask Questions


It's easy to ramble on about ourselves to fill the silences. Instead, bring a few questions along with you to stimulate new directions for your discussion if things start to stall out. Consider asking about career achievements, interesting travel incidents, or even favorite movies, since you might even find some common ground or shared experiences with these topics as you get to know each other. 



5. Talk About the Elephant in the Room


Going on first dates can be exciting, stressful, and sometimes hilarious. Share an experience you have had as you jumped into the midlife dating pool and then ask about your date’s experiences. Commiserating about comical events or surprising dates is a light-hearted way to break the ice. Just be sure not to talk badly about any past meet-ups so that your current date will feel confident they won’t be fodder for such tales if this date doesn’t turn into anything more. 



6. Reach Way Back


Dating after 50 means that youthful school-aged years are in the distant past, but that doesn’t mean fond memories are. A lively discussion about “the way things used to be” can sometimes break the ice to help even the most different of people to feel a common bond in their similar or very different upbringings. 



7. Pastimes and Hobbies


Everyone has hobbies, interests, and activities that fill up their free time. Ask your first date companion how they fill their free time or spend their weekends. Not just a good compatibility test, understanding how a person devotes their time might suggest an activity you could share on any future meetups. 



8. Ask About Family


While you might already have a few details about your date’s family, a gentle prompt directing the conversation towards a broad term like “family” can lead to healthy discussions. Of course, watch for clues that indicate sensitive or complicated relationships that might be best left to future dates. But when dating later in life, the expectation that a family, children, or other loved ones have played a part in one’s life is a given. Opening a conversation to talk about meaningful family relationships is a great way to break the ice. 



Your Common Goal: Having a Fun Date

With a few conversation starters in your pocket, having a relatively smooth and enjoyable discussion on a first date is not too hard. But knowing what not to talk about, if possible, is also part of preparing for a successful first date. Probing questions about ex’s, divorce, why they are single, or financial stability are usually best left to future dates unless the topic comes up naturally in a conversation and it does not dominate the date. While no topic is really taboo, be sure to read the subtle or overt signs that your date doesn’t want to discuss a given topic to ensure you both have a pleasant time together. Above all, enjoy each meet-up as an opportunity to connect with someone new regardless of where it goes after the first date is over.


 Photo: mohamed_hassen/

Editor, 08/12/2021