Dating in your 50s as a Lesbian: Bring Your Wine, Your Floaties... and Maybe a Cat or a Dog.

Dating in Your 50s is a Comedy Show I Didn’t Audition For. (Now With More Lesbian Plot Twists)

Welcome to the jungle, baby.

Bring coffee, wine, and possibly a helmet! 

When I first dipped my toes (okay, cannonballed) back into dating, I had no idea what I was in for. I thought dating at this age would be easier. Wiser. More refined.Spoiler alert: it’s just weirder. It just got a tad unhealthy.   And somehow... so much funnier.

They said dating gets better with age. I’m here to tell you: it SUCKS and the unhealthy out there is unreal.  I am unsure how some women pull their luggage behind them; it is that bad. 

Welcome to dating in your 50s —lesbian edition– where every coffee date feels like a live episode of "What the Hell Just Happened?"

First, let's start with the basics:

In your 20s, you looked for chemistry. OR let’s just be honest, if they were hot, we were making out.    In your 30s, you looked for stability, or some, we still looked for the hot ones. In your 50s? You’re just looking for someone whose emotional baggage fits in the overhead compartment. OR let’s just be honest, we are still looking for the hot ones, but we have accepted hot to just attractive now.  Maybe somewhat in shape, has a job, doesn’t live at home, drives, has their teeth, you know all the things, and so much more.  

Some highlights of the experience thus far:

• The Profile Picture Time Machine: She looks adventurous, stylish, full of life... until you realize the photo is from her Indigo Girls concert... in 1997.

• The Fast-Forward Syndrome: First date? Who cares! Let’s talk about co-parenting, astrology charts, and whose cat is more spiritually evolved, or whose dog is the cutest (Spoiler: it’s always their cat, and they may come with 2 dogs.)

  
  

• The Ex-Factor (Squared): Not only will you hear about the ex... You might actually know the ex. Hell, you might have dated the ex. (The lesbian dating pool is not so much a pool as it is a very small, suspiciously murky hot tub.)

• The Text Dump (Yes, It Still Happens. No, We’re Not OK About It.)

You'd think after surviving decades of life, careers, heartbreaks, and raising teenagers (or cats, or dogs), we'd be too mature for ghosting and text dumping. You would be wrong. (This may have just happened to me)

Because somehow, even in your 50s, you can still get a "hey, I think we should just be friends" text —or, I love you, but let's take a few months. A few months? Is this the, I want to meet other people, and if it is scary out there, I will be back text? (Spoiler: ummmmm NO!)

AFTER you just bought her favorite vegan cheese and introduced her to your cat and or dog,  OR the day after your birthday, or a holiday, because that is how we all want to remember that ONE birthday or holiday. 

Sometimes there’s no text at all.

Just silence. 

A void. Ghosted. 

A spiritual disappearing act so complete, you're tempted to file a missing persons report.

Congratulations. You didn’t just date someone — you survived a Lesbian Houdini. (And if you’re lucky, you’ll never run into her at the co-op while buying organic coconut milk.)

•  The Lesbian Dating Pool: Now Featuring Familiar Faces

You go to a coffee date and realize you have 37 mutual friends. You’re one iced latte away from discovering you’ve both dated the same woman. Possibly... at the same time. It’s not a pool. It’s a hot tub. And it’s getting weird in here.

• The "Are You Even Real?" Encounters: There are moments where you genuinely wonder if you're being punked. Like the woman who said, "I'm emotionally available," then spent the entire date talking about her ex and how connected they are.   (Spoiler: she was not emotionally available.)

  
  

• The U-Haul Jokes Are Not Jokes: Straight people think it’s a punchline. We know it’s just... Tuesday. (“We had a great second date — she’s moving in Friday.”)

• The Emotional Resume Review

Before you even order coffee, you’re trading trauma timelines like trading cards. “I’ve been divorced twice, survived therapy, and once led a meditation group for women healing from narcissists.”  “Oh wow, same! Plus, I have a gluten sensitivity and three unfinished screenplays.” Perfect. Let’s trauma-bond... but make it sexy.

• The "Is She Flirting or Just Being Nice?" Olympics: Women are so nice. Too nice.

  You think you’re vibing. She’s smiling. She’s laughing at your jokes. You share playlists. You swap favorite vegan restaurants. You spend three glorious hours bonding over childhood trauma, kombucha brands, and your mutual disdain for cargo shorts.

  Naturally, you start thinking, "Wow, this could be something."

  And then... nothing happens. No flirting. No obvious signals.Just vibes. Endless, wholesome, utterly confusing vibes.

  Because in lesbian dating — especially over 50 — it takes three separate dates, a shared playlist, and a full camping trip to confirm she likes you...Not just your energy. Not just your dog. Not just your taste in overpriced vegan cheese. YOU.

  Honestly, it’s an extreme sport at this point.

  
  

• The Positives (Yes, There Are Some!): 

  You know yourself. 

  You know what you want. 

  You’re not afraid to say "no thanks" politely after one drink — or to ghost with dignity if necessary. 

  And you laugh. A LOT.  Sometimes with them, sometimes at them, sometimes alone in your car afterward, wondering if that date counted as a relationship under lesbian law.

  
  

So here’s to lesbian dating over 50: Where coffee dates or wine dates turn existential, everyone has an ex in common, and somehow... there’s a lot of laughter, love, and second chances.

Just don’t forget your floaties. And maybe an emergency cat treat or two. 🐾

We all need to find some humor in this world of dating, it isn't easy.. AND there’s nothing quite like the experience of online dating over 50.

You agonize over your bio ;

Too serious? You sound boring.

Too funny? You sound unhinged.

Too honest? You sound traumatized.

Finally, you land on something like: "I love the outdoors, good books, deep conversation, and not being ghosted again, thanks."

You go in hopeful. You go in open-minded.

You come out wondering if maybe it’s just time to buy more dogs.

Because here’s the thing:

Dating at 50 isn’t about finding someone to complete you. It’s about finding someone who doesn’t make you want to move to a cabin in the woods and live off-grid with only your dog or dogs and cats at this point, and bad lesbian poetry or a rerun of the entire L-word series. 

And if you can find someone who makes you laugh, kisses your forehead, and still has all their teeth intact?

 Congratulations. You’ve won the lesbian dating lottery. (Or at least you’ve earned the right to tell an absolutely killer story at brunch.)

At the end of the humor, dating has much to offer; it is learning to :

• Speak your truth without apology

• Walk away when something doesn’t feel right

• Laugh through the awkward moments

• Stay open, even when it would be easier to shut down

• Choose connection over perfection

Dating over 50 teaches you things no self-help book ever could: Patience. Resilience. Self-respect. Hope. Humor. And most of all — a deep knowing that you are already whole. With or without a relationship.

When you date from this place — a place of wholeness — love becomes a bonus, not a rescue mission. The right person isn’t someone who "fixes" you. They’re someone who walks beside you, honoring the journey you’re already on.

And you? You get to keep growing, laughing, learning, loving — no matter what.

Whether you meet your match today, tomorrow, or on the next camping trip where you're still not sure if it's a date...you’re already winning. You're already walking the most important love story of all — the one with yourself.

Becky Shaffer

www.liveinconfidence.com