Dear Eligible Middle-Aged Man: You didn’t get a second date because…

October 21, 2023

Dear Eligible Middle-Aged Man: You didn’t get a second date because…

May 29, 2023

Dating at any age is fraught with challenges. Dating in your fifties (and beyond), however, has its particular issues. And I’m not talking about the usual complaints about the size of the male pool versus the number of available females, or the “age-appropriate” question.

Rather, my experience stems from having gotten started parenting relatively later than most, so I’ve only recently emptied my nest. I’m also self-employed in work that I love, which I have no intention of abandoning for days of golf and gin rummy any time soon. So I’m fully engaged with life, and therefore don’t have much in common with the sixty-something men who, anticipating retirement, might be looking for a companion of similar age.

I try, though. I ask friends to set me up. I’m online. I go to events and places that get me “out in the world” (when it’s possible to do that safely). And every once in a while I meet someone that seems interesting enough to go out with — who seems to find me interesting as well. Unfortunately there is rarely a second date, even though (I think) the recipe is really quite simple.

Here are a few of the real reasons why I declined a second date with some apparently lovely men;

  1. When I inquired about the kids you mentioned in your online profile, you showed me pictures — but disclaimed that the pics are out of date because of the restraining order. Seems your former wife thinks you have an anger problem.
  2. When I speak proudly about my son and his professional esports accomplishments, you follow up with a helpful article about the evils of gaming.
  3. You haven’t had any children of your own, but desperately want to be a grandparent. You dismiss me as a possible companion when you hear that I hope I am not a grandparent for another 20 years (my oldest was 16 when we had this conversation).
  4. You need to plan our meeting around the television program you “always” watch every Sunday.
  5. My polite inquiry about your day leads to a long discourse on the reasons why your ex-spouse had no reason to suspect you of criminal behaviour with that client.
  6. The outbound message on your home phone is still in your deceased wife’s voice, five years later (so sad).
  7. The tank top you wore to our first date at the art gallery tells me you didn’t give thought to showing up at your best (or if that IS your best….!!).
  8. Our introductory coffee meeting was essentially an interview, assessing my intentions and suitability.
  9. Your long-term marriage ended very recently — and not at your initiative. Give it some time…
  10. You’re busy, but can squeeze me in three weeks from Thursday…
  11. You don’t want a “relationship” because you “value your freedom.”

If you’re too entrenched in your routines and habits it will be difficult for a new person to find space in your life. And if you haven’t done your own work — if you’re still carrying a lot of baggage — then you’re likely to repeat the patterns that didn’t work in the past, which probably won’t appeal to someone new.

All that said, if getting to a second date is a challenge there need to be more first dates — awkward as they are. Yet I struggle to find many that I want to “swipe” in the appropriate direction. As a bit of a guide to those of you gentlemen who are wondering why you’re not having much luck online, here are a few tips:

  1. No bathroom selfies. It’s just creepy. Ditto shots with that rumpled, unmade bed in the background.
  2. Lose the sunglasses. We want to see your eyes.
  3. Smile.
  4. Motorcycles are polarizing — women love them or hate them, so you’re quickly reducing the size of your interested audience when you feature yours in your photos.
  5. Ditto fish, fishing and hunting. It’s not necessarily a problem to have these interests, just be thoughtful about whether you want to lead with them.
  6. While I love that you have friends, if I can’t tell which one is you in the group photo it’s not helpful.
  7. No details or personal commentary in your profile? While online dating isn’t perfect, it’s what we’ve got — and if you won’t take the time to write something about yourself I suspect you won’t make time for other things that require a bit of thought and effort.
  8. Ditto making time to meet. Your willingness to create opportunities for us to see each other tells me everything about how badly you really want someone in your life.
  9. If your beliefs about relationships are such that you find them confining and restrictive, we’re probably not looking for the same thing so please appreciate that I can see that and want to move on.
  10. Ask me questions. Questions indicate a genuine curiosity about who I am. PLEASE express interest in me as I do in you. Feeling seen and heard is important to us all.
  11. And last but certainly not least — consider dating women your own age. I promise you, we’re interesting, interested, adventurous (in a great many ways!) … and we’ll get your jokes and like your music!!


It’s tough out there, but I remain optimistic! And I welcome helpful suggestions.

- Karen

Karen Wright is an executive coach, two-time MEA alum, and single “older” empty nester who is still hopeful about love. She can be found on dating apps looking for self-aware, thoughtful, monogamous men aged 50-70.

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