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10 Dating Questions: A Man’s Perspective on Exploring Dating After a 28-Year Marriage

By Andrea McGinty May 09, 2024 Dating

You may be surprised to see such an article published on Sixty and Me, but please bear with me and read on to find some helpful insights into a man’s perspective when it comes to dating.

This was written (and not subsequently edited by me, Andrea) by my client Nav, a 58-year-old doctor who lives in Nashville. On my own blog I share a monthly column with insights from clients who talk about their experience with online dating and working with me – and how it all turned out.

I’ll let Nav tell his story through a series of questions:

What Was It Like to Be Single After Being Married So Long?

It was a bit disconcerting. Having been married for 28 years and then suddenly be thrown into a reality where you are entering the dating world in a different decade and having to juggle multiple responsibilities (career, kid). The nice thing was now you had the means to enjoy the nicer things in life, but time management became much more of a factor. Balancing a busy career and dating was a challenge.

What Made You Decide to Call a Dating Coach?

I remembered an article written in the WSJ about professional individuals, like myself, who found themselves thrown into the dating scene for which they were wholly unprepared. They had found that a dating coach was very helpful to navigate the new reality they found themselves in.

I interviewed a few coaches I had found online. Andrea seemed to be the most down to earth and informative. She took the time to find out what I was looking for in a partner, narrowed down the choices of which dating apps would be the most helpful in that search and helped me write an essay and choose the pictures that would give me the best chances of being successful on the online dating scene.

Andrea was also was very helpful with the dating process itself after I had gone live online. With her vast experience and knowledge working with thousands of singles (both men & women) she provided valuable insight into how women think, how they react to situations differently then men.

It was like having a radar on a plane. She was able to reliably forecast how my dates would proceed and guide me during my journey.

How Many Dates Did You Go on Since Single and Any Funny or Weird Stories? Did You Ever Want to Give Up on Dating or Online Dating?

Went on several dates with women I met either at work or friends/coworkers had arranged. Went out with about 8 or 9 women I met through the dating apps (only tried Bumble).

Some interesting stories:

Golf Woman

My profile clearly stated I loved the mountains, active adventures, and Golf. Spoke with a woman on the phone (thru Bumble where the woman initiates the contact) who proceeded to talk nonstop for 45” (I got 12 words in… I counted). She related to me that she is a beach person who hates the mountains, Golf is a boring sport (she actually said, “I would rather watch paint dry.”) and would rather sit by the pool than do anything active. I was thinking to myself, Why did you even reach out because that is the anthesis of what I am or what I am looking for?

At the end of the phone conversation, I told her that it was nice to speak to her, but didn’t see a lot of commonality so good luck with her dating journey. Got a text later that night that asked what turned me off? Was it the Golf?

T-Rex Woman

Another story is a date where the woman asked me on the phone whether I liked dinosaurs. I replied, “Sure, who doesn’t like dinosaurs.”
When I went to pick her up for our date, she greeted me wearing an T-Rex outfit and nothing else. Lol!

What Number Date Was Heather and How Did You End Up Choosing Her as a Date? What Happened Leading Up to Your Date with Heather and What Did You Do on Your First Date?

Heather was probably the 8th or 9th individual I had gone out with. I liked her smile in her pictures and her written profile. It was very down to earth and both showed she did not take herself very seriously. We had a great conversation on the telephone. We went to dinner the first night. Subsequent dates we went mountain biking, rock climbing, and golfing.

Photo credit: Nav Randall; image provided by Andrea McGinty.

Did You Know She Was the “One” on Your First Date? Was There Instant Chemistry?

There was definitely chemistry, but no, I didn’t think she was the one on our first date. Did think she was an interesting woman with a great life story who I would like to get to know better.

When Did You Meet Her and How Long After Did You Propose? How Did You Propose?

We met in Mar 2021 and got engaged in Sept 2022. Went to Switzerland and did a hiking trip. During which, right at the beginning of the trip, she broke both her hands in a Trotti Bike accident (basically, a Razor scooter that kids love, which you take on downhill trails). It sounded like a sketchy idea and turned out to be not the best idea we had. This accident would have ended the trip for a lot of people; however, her positive attitude and desire to make the best of any situation allowed us to continue with the trip.

We modified the trip to do less strenuous hikes and less miles each day, but she really showed her character in the face of the adversity and confirmed for me that I had made the right decision in my life partner.

What Did You Like About Heather?

Her positive attitude towards life (glass half full vs half empty), her curiosity, empathy, importance on relationships with family and willingness to try new experiences.

Tell Us a Little Bit About Common Interests/Different Interests and What You Like to Do Together

Quality time is our love language, and we enjoy spending time together. Whether it’s a daily walk in the evening with our dog, or having dinner and then watching TV for an hour. We also enjoy riding bikes together and traveling. She is a true teammate and makes life just easy.

Did You Ever Think You’d Remarry? What Advice Would You Give Someone About Online Dating?

Did not think I would remarry. But luckily found the right individual who had the essential core values I value and the personality that meshed. That is a hard combination to find.

Would say definitely try it, but enter into the experience with a positive attitude and not a whole lot of preconceived expectations. Every date is a new opportunity to have an interesting conversation and experience. You can always learn something with each date be it positive or negative. It was interesting meeting accomplished women who themselves had amazing life experiences.

Be inquisitive, but don’t make it a job interview. Also would say Andrea’s advice of “meet someone don’t text” was spot on. After a few texts, I would say, “I really prefer to talk to you.” If the phone conversation went well, would suggest a place to meet.

Also realize that life is not a Hollywood movie where you meet someone and there is an instant attraction and you know immediately that “this is the one.” Give someone who you had an interesting date/conversation with, but didn’t check off everything you were looking for another chance. There were multiple times when I found the 2nd or 3rd date to be better than the initial date.

Tell Us About Heather and How the Relationship Progressed. When Did You Know for Sure She Was the One?

We went on 4 dates while I was dating other women, and she was dating other men. (She had a rotation of 3 men, she said “that was all she could keep straight at one time” LOL!) I had no idea that I was part of a rotation.

Both of us quickly realized that when we were going out on other dates, they didn’t measure up to the compatibility and chemistry we had with each other. We decided to go exclusive after about 3 months of dating and then went through some major events in both of our lives (my mother passed away unexpectedly, and Heather had a major surgery an ACL repair on knee she injured during skiing).

In a short timespan, these events showed how each of us handled adversity. This insight into each other’s coping mechanisms and the support we provided each other during these hard times made us realize how compatible we are with each other. Also, we both learned something from our previous relationships and made it very intentional to not make the same mistakes.

A very good exercise we did while dating was reading a book by John Gottman (8 Dates Essential Conversations for a Lifetime of Love). We each read a chapter and then went on a date to discuss that particular chapter. The book really covered all the topics that should be discussed prior to entering into a long-term relationship and gave me valuable insight into Heather.

Editor’s Note: Top photo credit by Nav Randall; image provided by Andrea McGinty.

Let’s Have a Conversation:

Do you think women need more insight into men’s attitude toward dating? Are you nervous about dating after a long marriage? What did you like about beginning dating again? What are some of your favorite dating stories?

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Nice article. I have another issue and I don’t know where to post it for possible suggestions on how to handle a situation. I met a man online who lives in another city (about 60 miles away). We get along well on a lot of levels. However, from the beginning I told him I was not interested in marriage or living together. Over the last eighteen months he has become quite serious and I’m not. I know that he is ‘not the one for me’. I don’t want to continue the relationship – as I feel it best he move on and find someone else. I don’t want to hurt him, but feel it is best if we moved apart. I want to be gentle, but somehow I just can’t formulate the words to tell him. We have also become good friends. Suggestions?


Can you tell him that you’ve met someone else? You say you feel it is best that you move apart—I’m hoping that you aren’t actually living together, coz that will be more difficult to do—but you could be busy with a new man, & simply not have time for this guy who lives 60 miles away. Be strong. Good luck! 🇦🇺

Lynne Stevens

My one and only experience on a dating site wasn’t very successful. Generally, all my life I have found that men about seven years younger (or older depending on my age at the time) than me were just about right, but I also found that the men my current age wanted a younger woman, the men older than me wanted a younger woman to spend their “twilight years” with (sounded like they were looking for caretakers), the men I was interested in were active but didn’t contact me. A lot of them looked at my picture and profile, but since I look a lot younger probably assumed it was an old photo, that I was lying, and never went further than that. A friend of mine suggested I lie about my age, which is what she did and got lots of dates but no relationships. That made no sense to me to start with a lie before you even begin, so I just gave it all up. I live in a semi-isolated city in Alaska, been divorced for over 25 years and don’t expect any changes in status.


I also look much younger than my age. When I used to put my true age in my dating profiles, I had to read critical messenges from men who insisted that my current photos were 10 years old. So I started shaving 4 years off my age in my profile. I learned that so many people, both men and women, shave at least a few years off – some shave 10 or 15 years off. So hardly anyone I talked to was bothered when I told him my true age; and I always disclose that very early on. I think the problem comes when someone actually does look their age but they lie about it and they also use outdated photos. That’s very different. Men would still be amazed when they learned my real age because they thought I look 10 years younger than I really am. But at least by shaving off 4 years in my profile, it made my photos seem plausible and reduced the number of hostile messages I would get when men questioned how old my photos were

Last edited 12 days ago by JLS

I’m glad I’ve never done online dating – or any! I look much older than my age in my own opinion as I’ve had a ton of stress in my life. Or at least my neck and facial skin look horrific. My body, though I’m 20 pounds more than my lifelong 112, I guess is maybe the only part that does look my age.

You two are lucky that you look younger! Wish I did too….


Thanks for this interesting and inspiring story. But I must point out that because women get so many more messages than men do – including a lot from men who don’t read profiles- the only way a woman can avoid wasting time on umpteen dates every month (and most of them will be bad dates) is to do a considerable amount of screening via texting first. I don’t see what the downside is in screening that way. I met my late husband on a dating site. Then later I had a significant relationship that lasted a few years since my husband passed away – we also met on a dating site. I have always screened carefully with a lot of texting before a phone call. While this was an inspiring story of Nav’s success in falling in love and finding a new wife, it’s going to be very different for women on dating sites, particularly if her profile is very appealing

The Author

Andrea McGinty is the founder of It’s Just Lunch dating service. She sold it and founded so she could help singles navigating online dating. In the 2020s, she knows the best way to meet people is through online dating using a professional coach and specializes in singles in their 50s-70s!

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