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Two Men Reveal Their Thoughts and Strategies About Online Dating

By Andrea McGinty November 29, 2023 Dating

All day long, I help my clients with online dating and hear some interesting perspectives. Today, I am featuring two men who went through the online coaching program with me and who agreed to an interview to share their thoughts, ideas, misgivings, feelings, and advice to others on online dating and the best approach.

But Wait – I’m a Woman!

I’ve heard an interesting observation from many female clients regarding potential dating partners. It goes like this: “Oh, no, Andrea, not him. I’ve seen him online for 5 years.” First, let me say this: you’ve been online looking for 5 years yourself – with no success – yet you won’t reach out to a man in similar straits??? Well, just wait!

Back to My Interviewees

These two men, just like many of my clients, had one thing in common – they wanted results, and they didn’t want to spend much time messaging women online. One commented he’d rather be on the golf course than on a dating app; the other has an intense career and in his free time he plays basketball – neither’s idea of fun was online dating.

Surprise, surprise, right?

I’ve changed their names, of course, and for simplicity, here are the facts:

Mark, 64, a business executive from Dallas who travels 85% of the time and so has serious time constraints.

Tim, 68, Silicon Valley, technopreneur and founder who lives primarily in New York City.

Here we go with the interview:

Why Did You Decide on Online Dating?

Mark: I realized I wasn’t going to meet anyone where I worked. I was highly discouraged plus I was a high-ranking executive at a Fortune 100 company. I’d been divorced for 5 years – had two teens at home – and I was just ready to date (not a serious relationship, I thought). I knew nothing about online dating but had seen commercials.

Tim: I didn’t see any other choice. Everyone is doing it! I looked at the company you founded, Andrea, It’s Just Lunch, and just couldn’t imagine they had a large enough pool compared to the internet. Seemed a no-brainer when I researched the numbers on the online dating pool.

Feelings About Going Online?

Mark: Hesitant; fearful of people recognizing me, and it happened twice – a woman from my neighborhood who I actually went on a date with and a woman from my company who I did not go on a date with). At this point, I got over my fear of people recognizing me. I thought, “Hey, our senior VP of Marketing is online.” So I got over it!

Tim: My hesitation was privacy – people will see you unless you choose the option where they only see you if you select them, but then you are limiting your options. Another drawback was time; not to get caught up looking at these damn sites all day long. Well, I did do that until I hired you and you wouldn’t let me. (He laughs).

How Long Were You on the Sites/Apps Before Reaching Out to a Coach?

Mark: 5 years. I just had no time and would check it once a month – which of course was not optimizing my dating life. I went on maybe 4-5 dates a year, but wasn’t putting much effort in. Then my kids went off to college, and I hired you and got more serious. I didn’t even know someone like you – a dating coach – existed five years ago. Hey, I was married a long time!

Tim: I was married for 24 years and initially got lucky online and was in a relationship for 9 months. I then went on 3 sites/apps for three months which was overwhelming and that’s when I decided I needed help and hired you to vet these women and show me a more efficient way to use online dating.

How Often Did You Check the Dating Site/App?

Mark: Once a month.

Tim: Every day before you. I’m super organized and tend to check emails constantly too – but I quickly got swamped with the dating thing and got discouraged/frustrated with the time and energy it took.

What Three Things Make a Woman Attractive to You So You’d Want to Reach Out? And, How Did You Respond – Message, Phone, Straight to a Meet?

Mark: Her photos, and if something in her profile made me laugh, or we had a commonality (like one woman also was from Boston where I grew up and visited the Cape often, as I do). A message on the app, then a text on the phone, then a short phone call. I did the phone because I’m a bit reticent and shy – so by hearing their voice first it made the in-real-life meet really feel more comfortable and almost like a second date.

Tim: All the things you preach: multiple photos, a complete profile, and listing things that are truly unique to them – no generic platitudes. As far as the first date, I think women want to feel safe, so I’d take the lead from them – I’d say 50% we just agreed via text to meet at a restaurant and the other 50% we had a short phone call after a couple of texts. It just depended on them.

Did You Ever Think About Using a Matchmaker or Doing Group Single Events?

Mark: Definitely not my style at all. I wasn’t comfortable with either of those.

Tim: No. In today’s world, it makes no sense. It’s like travel. Do you really need a “travel agent” these days or can you book your own hotel and flights? Now having someone write your profile, select photos, set me up online and help choose dates – that’s cost effective.

What About Your Photos?

Mark: Initially, I just picked a couple – one with family and friends also to show I was social. Full body. A few women told me men misled on height (I’m 6’2”), so I made sure there was a full body shot too. And I was smiling. You had me add more – no baseball cap and only one with shades on!

Tim: Typically, 5. Headshot, activity (at a football game or concert), hiking. Wanted to show full body in maybe shorts and t-shirt.

Any Advice You’d Give Women Who Are Online Dating?

Mark: Stand-out by saying unique or quirky things about you. I liked this one woman who said she loved hosting Thanksgiving each year for 40 people, and she did all the cooking herself – I was impressed as she sounded fun and ambitious with entertaining! Have a full body photo for sure – I did look for that. And make sure your photos are current, so men aren’t surprised. Oh, and be honest about your age too.

Tim: I frankly got mad when I met someone where it was obvious that they were using old photos. My advice to women: always date your photos.

Anything Else We Should Know?

Mark: Hire someone like you. It saves time and you’ll be on the right track.

Tim: My dog photo got a lot of comments! So did the one playing pickleball with my 15-year-old granddaughter though I covered her face. It’s just showing the real you.

Thanks, Mark and Tim

Ok, so want to know their outcomes? Mark’s in a serious relationship – as he told me early on, never say that you’d never marry again! Tim – he’s been seeing Gail for almost a year; they don’t live together nor plan marriage – but it’s a committed relationship.

My oddball career to family and friends for the past 30 years began in my 20s – I feel so lucky to have many wonderful clients – and I’m happiest when I hear people fall back into dating or love.

Happy Holidays all! It’s a happy and fun time of the year to date!

Let’s Have a Conversation:

How did you feel about the male point of view when it comes to online dating? Did you agree or disagree? How would you respond to the questions posed to the two interviewed men?

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You’re selling a service. What you won’t tell people is that the US Census Bureau estimates that each year, out of every 1,000 widowed men and women ages 65 and older, only 3 women (0.3%) and 17 (1.7%) men remarry (Clarke, 1995). So the odds are heavily stacked, and not in our favor.

Stephanie Bryant

It’s so tiring! I had a guy who was scamming, but I guessed it pretty quickly and blocked him. Apparently there’s a lot of that out there, sadly.


Thank you for writing from the man’s perspective of online dating and for sharing your tips, ( we need to see more than ballcap and sunglasses pictures, please!)
I also appreciate the advice about “long-timers” and the fear of “someone may recognize me” on the dating sites. Thank you!


I live in a city that is known as the hardest place in the country to be single and get a date. Kansas City! You think that getting a date if you retired is easy, but it’s not. I’ve been on three or four sites for the last two years and have gone out on four dates maybe five. I’ll be 63 in a little over a month and I have never been so discouraged. I’ve done the matchmaker thing and three out of the five scared me to death. You’d think paying that much money would mean you get better dates but it didn’t. I have not lost hope but I’m starting to reconsider my options. There is someone out there for everyone and my mother always said the day you stop looking the next day he’ll walk into your life. Ladies keep the hope alive and enjoy life until he arrives. I still attend the opera and the symphony and the museum alone or with friends, so continue to enjoy life. Thank you for the male perspective, it was enlightening.

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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