Sex and the Single Mom: My Tinder Vacation



It’s so much easier to be your best self on vacation. Your responsibilities are usually relegated to fun and relaxation. Maybe that’s what I was hoping for when I decided to set up a Tinder account a few weeks ago at a teachers conference in Orlando. If I could just relax and be my best self for someone, maybe I’d finally go on a good date.

In New York, I’d been on a rash of bad ones: Men who didn’t want to get serious because I had a kid, men who couldn’t hold intelligent conversations, and – worst of all – men who didn’t know how to laugh and have fun. So here I was in Orlando, kidless and fancy free; ready to go on my first tinder date and make my vacation memorable.

I signed on, picked pictures that were equal parts flirty and funny, wrote a bio about being here “just for the weekend” and looking for “dinner and maybe  some making out” so no one got the wrong idea. Then I started swiping. I was overly generous with who I would consider. After all, it was just a date. I wanted good conversation, wine, and laughs – maybe a hot kiss goodnight; I didn’t really mind what package that came in. So, I dropped all my usual prerequisites. You didn’t go to college? No big deal. We will talk about movies and music instead of books. You look kinda short? Cool, I can wear flats and slouch for one night. Your eyes are a little too close together? It’s Orlando, we can wear sunglasses.

I immediately got some responses. I was surprised at the sheer number of men who wanted to meet me. Was it the temporary nature of my profile? Did the men in Orlando like a little extra chub with their love? Or was I digitally projecting my best self? No matter which hypothesis was true, I was excited. I picked my top three suitors and started messaging back.  

“Hey, hot stuff. What’s fun in Orlando, besides me?”

“Want to hang out in my hot tub?”

“Where should we go for our first and only date?”

I quickly got bored with the staggered time in between less than titillating responses.



“You pick.”

I was here in sunny Orlando with my beautiful friend, one of the smartest women I knew. I had a new bikini to try on – because in the words of RuPaul, “If I don’t love yourself, how in the hell are you going to love someone else? Can I get an Amen?” And, that morning I had taken a ridiculously expensive cab to grab a box of wine which needed drinking. So, why was I waiting for a man to take me out? I put my phone down, brought that box of wine and my gorgeous friend to the hot tub, walked there in my bikini (no cover up, cellulite jiggling), and had a blast!

This vacation version of me was fun and carefree. She drank a little too much wine from the box, stayed in the hot tub far past the doctor’s recommended 20 minutes, and had great conversations – all without a date. Was she the best version of myself, though?


Being a mom made me strong and confident. I was silly to think that a great date would come out of me being any other variant of myself. So even though I wondered how childless, vacationing Keveney would be on a date; I knew deep down she would always be a lesser version me.

The next morning I woke up alone in my hotel bed, still in my slightly damp swimsuit (yikes!). I reached over for my phone, as I do each morning, and saw 23 new messages on Tinder. Wow! I was flattered but quickly held down the app and  deleted it. Did I really want to go out on even one date with someone who was into vacation Keveney? No.  I wanted someone who appreciated and wanted the strong, single mom that I was, even if she was more complex and less carefree.

So, I am off Tinder and back on the two other dating sites I use here in New York. I did add that photo of me in the bikini to my profile, though, and things are looking up!


  1. Great & funny read, as always! Who you truly are really is the best you, even if there are more cares or complex feelings in your everyday life!

  2. Way to go! The best convos come with those who actually matter to us and those people are not on first Tinder dates. I love the confidence you have in recognizing and being your best self with your best self. I think she’s a pretty awesome self too 🙂

  3. It’s so nice to able to learn about your different sides. It’s not a bad thing to be vacation Keveney just like the more complex Keveney is amazing. We often feel so pressured to live in our self determined and society enforced boxes…screw that. That experienced helped you realize something about yourself so it was something you needed to have. Flaunt you hot bikini wearing self and love it! Any man that doesn’t can take SEVERAL seats and the one who does can truly appreciate it. I am not a mother but if I was I hope to be even a third of the mom you are!!

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