Something always gets in the way of dating

Tuesday | January 6, 2026

Love Letters Dating

Something always gets in the way of dating

What’s on your mind about your relationship life in 2026? Friendships, romantic relationships, family? Send an anonymous question through the form – or email [email protected].

I’m hoping the readers out there can help me. I am an attractive, fully employed, woman in her mid 50s. I have been single for many years now. I went through a very bad break up with a man several years ago, and since then, just haven’t met anyone who sparks my pilot light.

Each time I think I am ready to date, something BIG happens to get in the way (Covid, new job, loss of loved ones). I’ve looked at the apps, but I never seem to get past the talking stage.

I am active in my community and very friendly to everyone I meet. Is it because of my age? I’m well past menopause. I don’t want to be a “nurse or a purse” as my friends say. Are there any attractive, well-established, single men out there? Is there possibility for romance at this stage in my life? Help!

– What next?

Yes, romance is possible. Yes, there are men out there – even on dating apps.

These apps can make very wonderful people look worse, I fear.

Profiles can turn humans into something more … two dimensional. Quick conversation can feel stilted, and then both parties lose the will to send the next message.

Some singles are simply bad at showing their best selves on dating apps. You might be one of them.

Find a new app. A different platform might yield better results.

After you join this app, show a savvy friend what you’re up to. See if they have notes/constructive criticism.

Then start asking people out. Get to that first date quickly by saying, “Let’s get together.” Or skip that part and try a FaceTime call.

Consider widening your mileage range on the app. If you’re dating people within a 15-mile radius, make it 60. Some of the most dateable people fall outside of our arbitrary lines, and I have always thought, in Boston, “Wouldn’t you be so excited to fall in love with some adorable person in a small town in Maine?” (That’s my rom-com brain talking.) But really, people who are serious about finding love will drive.

Last thought: I would never suggest forcing yourself to multitask – especially as you cope with the loss of a loved one – but I do believe that busy times/weird times can be excellent moments for dating. Why? Because it’s all low stakes. It’s like, “Everything is strange, rushed, and out of order, so why not message some man?” If it doesn’t work out, it’s no real loss. If it does, someone gets to know you during a very authentic moment. That can be nice.

My point is, “I’m busy and dealing with a new job” might be the best time to force yourself to send a few extra messages.

– Meredith

Readers? Advice? Open to sharing your own experience as a 50-something dating? Thoughts on nurse/purse and what it means to be well established?

What’s on your mind about your relationship life in 2026? Friendships, romantic relationships, family? Send an anonymous question through the form – or email [email protected].

Dating Dating fatigue

Featured Comment

If you’re going to focus on using the apps – just be really open minded since some people aren’t great at selling themselves in 250 characters. Everyone is dealing with job loss, family health issues, etc but you can still participate in life even while these things are happening.

surferrosa Share Thoughts