Pickleball, Dinner With Cupid, and 'sufficient lovers'

Friday | June 27, 2025

Love Letters Dating

Pickleball, Dinner With Cupid, and ‘sufficient lovers’

Hi Meredith!

When I was 75, I think (I am now a 78), I sent a long completely filled out questionnaire to [Dinner With Cupid] hoping that I would get a date out of it. That never happened. And I get it, how many men suitable at my age could be also applying?

Here’s my question: married twice, widowed the first time, divorced the second time. I will admit I’ve had sufficient lovers, have been busy, lucky with friends, grandkids, and pickleball. But I’d still like to have one last love fling before I die. I don’t actively search for this; it’s just something in the back of my mind. I don’t have a bucket list, but if I did, this would be it. Any advice?

– One Last Love

Look for this fling. Please.

Get on an app and tell people you have a full life (pickleball included), but are searching for another love story.

What a magnetic, honest thing to say.

“I like pickleball – and romance.” Be direct because … why not?

I can’t promise you a zillion suitors, but what a fun project – to see who responds to your very clear casting call.

Allow for a wide age range – because again, why not? If you have a friend who can help you screen, that would be nice. Also: Don’t give anybody any money. That friend/family member can help you with a vetting process.

My last thought: break out of your inner circle just a little. If you have the chance to play pickleball with strangers, go for it.

Now let me say to everyone else: if this person sounds great to you (or might to a family member), apply to Dinner With Cupid and say so. We will make this happen. Dinner. Pickleball date, maybe. Let’s do this thing.

– Meredith

Readers? Advice for the search? Pickleball and dating? Know someone for this LW?

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Featured Comment

DO actively search for it! It sounds as if you have a lovely life, keep enjoying it, but maybe be willing to go out on one date a week? … Date people from the suggested apps geared towards older people, or from meeting through friends, or maybe from meeting through a social group/event such as pickleball. Take risks and flirt, be the one to ask for a date instead of waiting to be asked, worst case scenario the person says no, oh well! Enjoy!

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