Sex and The Single Mom: My First Date After Baby


dateIt was summer, and my son was less than a year old. I’d lost the baby weight (don’t get me wrong, I still had all the weight I’d carried pre-baby, but I was feeling myself sans swollen ankles and elastic waist pants) and finally felt ready to date. A month or so before, I’d made an online dating profile and bought new shoes, hoping for the best. I thought I’d found it.

In the mommiest of mom moves, I scheduled a job interview at 2 p.m. and a dinner date at 5:30 p.m. (one babysitter, two stones, as it were). In retrospect, I picked an outfit that was a little too sexy for an interview but a little too bland for my date and rode the subway to Harlem. The interview went swimmingly, so I was running a little late for the date. That, plus the new shoes, led me to take a $7 cab ten blocks to the little Cuban restaurant we’d agreed to meet at.

Standing in front were several strangers and one person who looked kind of like the man, let’s call him Too Good to be True, whom I’d been talking to online for weeks. So, when I exited the cab, I waited on the curb to see if it was him or perhaps a long-lost, shorter, and younger cousin.

It was him. I’d thought that building familiarity would allow me to feel more comfortable on this “first date since baby.” Instead, it built my expectations to gargantuan proportions.

I loved everything this guy had to type. So seeing that he was shorter than I am (a deal-breaker for anyone who’d ever tried to talk to me in real life – and not what was listed on his profile) and that he was sporting what I could only assume were a new set of adult braces – made my heart sink. I shook it off; the attraction could grow. I attempted to maintain my excitement about our date.  

That ended as we were handed menus. He explained his IBS causes and symptoms to me to understand why he was only ordering an appetizer at the restaurant I picked out. “We can go somewhere else,” I offered. He assured me it was fine and that he enjoyed the live music playing, so he would eat when he got home. I ordered just an appetizer in solidarity, and we waited in silence.

“I guess we already texted about all the important stuff,” he joked. I agreed. The questions lingering in my mind weren’t first-date conversation starters (in fact, they were probably date enders). So, instead, I told him about the interview I just went on, showed him the newest, cutest pictures of my son, and then sent a prayer to each God I could remember from World Religions class that the food would come quickly.

It did, and we ate. I thought mine was delicious, but after a few bites, he pushed his to the side. “I think there’s milk in here.” I didn’t think beef empanadas could contain dairy (an IBS no-no, apparently), but he seemed sure. I was starving and offered to eat the untouched half. At this point, my typically demure first date personality was safely locked away, ready for someone else; I had transformed into my true self: an unabashed, ravenous foodie. I cracked jokes and laughed openly at them; I talked to the lovely, older couple sitting next to us (tables are too close together in NYC, am I right?), and the night generally began to improve.

Too Good to be True excused himself to the bathroom. I continued to talk to the couple next to us. It was their anniversary, 21 years of marriage, and they were both smiling. I wanted that. I knew it wouldn’t happen with this guy, but maybe the next, or the guy after that. If my life could look like theirs, I was committed to trying to find “The One.”

My date was still in the restroom 20 minutes later, and I surmised that he’d either run out on the check or there really was milk in those empanadas, and he was dealing with their effects. “It’s the first date; I don’t think there will be a second one,” I said to the wife sitting next to us. She smiled, but her husband adamantly agreed, “Trust yourself. When you find the one – you know.” I continued to ask them questions about life and love. I even danced with the husband (the wife’s knee hurt) before “Too Good to be True” returned.

“Let me take you out for dessert,” he suggested, wanting to make up for his long absence and the fact that I’d already paid for our meal (or appetizers as they were). I agreed because I was hungry and felt like I was owed something for sticking around this long. He took me to Dunkin Donuts. Maybe that was more his speed because while there, he opened up. Unfortunately, it was about how he once beat up his sister’s husband, his mother’s memory loss, and how often she’s mistaken him for his dad, and finally, about all the parts of a woman he missed because of a dating drought. At the end of the night, I escaped his lunging for a handful of one of those parts by hopping into traffic and hailing a cab. “Have a good night!” I yelled out the window.

As we sped up the West Side Highway, I made some rules for myself and all future dates.

  1. Never talk to someone for more than a week without meeting in person.
  2. Ask for “recent” photos. If all he can produce are less than five from his profile, he probably doesn’t look like that.
  3. Mention any pet peeves. I always say that I can’t date someone shorter than me and let him know it’s about me and my insecurities about being a giant (really, when I was traveling in Ecuador, a small child called me Godzilla), not them.
  4. Save some of the first date conversations for the actual first date. Too often, we get comfortable with someone through an electronic device, and that’s no way to build a relationship.
  5. Last but certainly not least, trust your gut. If it’s saying this is wrong – then it is – and there’s no reason to give more of your precious time away. Save it for “The One” or at least someone fun along the way to finding “The One.”


    • Thank you! They seem to work even if they don’t elicit amazing dates they make me feel better about my dating decisions.

  1. I am so with you on meeting sooner than later! If there’s too much chit chat you can’t get to know each other IRL. The One is elusive and sly though. Haha


Please enter your comment!
Please enter your name here