7 First Date Conversations Senior Women

Senior Dating

7 First Date Conversations for Senior Women

Nick Slade

Written by: Nick Slade

Nick Slade

Nick spent 20 years in the dating scene before marriage. He has always been the guy friends would come to for advice on relationships, and he developed a knack for giving helpful insights. After college, Nick was a disc jockey for a few years, when the love generation was still alive, so Nick has a lot of relevant experience to draw from when it comes to every aspect of dating, falling in love and screwing things up. He holds Bachelor's degree in humanities and a slew of master’s credits in journalism. Nick is a news junkie and tries to keep up on the latest non-fiction when he has time. He has published two books on how to win at dating and relationships.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Discuss This! Discuss This!
Advertiser Disclosure

Even two people with a lifetime of experiences can hit a road block when first date jitters cause them to draw a blank on topics for conversation. So, it’s a good idea to have a few ideas up your sleeve to keep the chatter going smoothly on that important first official date.

Comparing irritable bowel symptoms with Jeannie next door may be a stimulating topic at home, but you don’t want to find yourself falling into disturbing topics with your potential new beau.

1. Past conversations.

This might be your first date but it’s not the first time you’ve interacted with each other. You’ve talked on the phone, chatted online or had a few words when you met at your friend’s house or at church.

You know enough about each other to bring you together for a date, so draw from those past conversations to get the talking started. Think about how or where you met, and dig into that. If you met through a friend, ask about how he got to know that person and what kept them together as friends.

If you met online, ask about what sites he likes, how long he’s been using the Internet, and what he thinks about it. That can branch off into a conversation about his computer skills, the kind of computer he uses, and what he uses it for.

2. His career.

Every man loves to talk about his work, where he worked, what he did, how long he was at a company. Of course, he may start getting into details way too small for your level of interest at this point, so be sure to have another topic ready to bail you out.


“Tackle the fun topics first, and then

work toward the more sensitive issues.”

3. His hobbies and interests.

He might love golf, football, gardening, remodeling bathrooms, or building furniture. He may like to cook, grill outdoors, read spy thrillers, or collect old movies on DVDs. Try to tap into his passion and figure out why he enjoys certain things so much.

If his interest seems like something you would never think about pursuing, that can make it even more interesting for you to learn about. And it will reveal a lot of good insights into his nature for you, too.

4. His family.

Families can be a sensitive topic or a source of great pride. You will be able to tell right away if the topic is to his liking or not. If he shies away from questions about his former marriage or kids, ask about his own childhood and siblings.

You don’t want to pry or go into too much depth at this point, but you might learn a lot of useful information about your man. Also, whenever he says something about his son, the tax accountant, don’t counter with a story about your son, the doctor. It’s not a competition!

5. His travels.

Everybody has been somewhere. Find out what places he has visited on our planet, foreign or domestic.

  • Why did he go there, and which spots did he enjoy the most?
  • Does he plan to do more traveling?
  • Does he enjoy an occasional road trip to visit family or just to have new adventures?
  • Does he prefer to fly or drive?

6. His accomplishments.

His greatest accomplishment might be raising children and sending them to college, beating cancer, rising from the ranks to become a manager, or maybe something that will totally surprise and amaze you. It will tell you about the things that really matter to him.

7. His dreams.

Ask him where he would live if he could live anywhere. Find out the places he would really love to travel to. Find out if he has anything left on his bucket list.

Every man has dreams and aspirations, and few of them achieve everything they hoped for. Share his dreams for a while, quell his regrets, and make him believe once again that anything is possible.

If you like the man and truly want to get to know him better, ask him the things you want to know more about. Tackle the fun topics first, and then work toward the more sensitive issues. You may or may not have a lot in common with him, but you’ll never know until you ask.

Advertiser Disclosure

DatingAdvice.com is a free online resource that offers valuable content and comparison services to users. To keep this resource 100% free, we receive compensation from many of the offers listed on the site. Along with key review factors, this compensation may impact how and where products appear across the site (including, for example, the order in which they appear). DatingAdvice.com does not include the entire universe of available offers. Editorial opinions expressed on the site are strictly our own and are not provided, endorsed, or approved by advertisers.

Our Editorial Review Policy

Our site is committed to publishing independent, accurate content guided by strict editorial guidelines. Before articles and reviews are published on our site, they undergo a thorough review process performed by a team of independent editors and subject-matter experts to ensure the content’s accuracy, timeliness, and impartiality. Our editorial team is separate and independent of our site’s advertisers, and the opinions they express on our site are their own. To read more about our team members and their editorial backgrounds, please visit our site’s About page.