Online Dating & Single Motherhood: I'm Giving It a Try!

Dating. What can I say? Dating as a single working mom with no participation from the father (who is married with a child) is … hard. I have no nights or weekends off like my other single parent friends. I don’t have much time to hang out at happy hours, and I’ve found that dating people that live in my building is more trouble than it’s worth (oy). I spend the majority of my time taking care of JD, doing kid-friendly things and working in a mag office. I have a ton of married and single parent friends, but our time together is often spent drinking beer in someone’s yard while our kiddos slip ‘n slide. I spend time with my fam at the beach and for Sunday dinner.

There’s the beautiful notion a single parent will meet someone while they’re pushing their kid on a swing or feeding an animal at a petting zoo … or while wearing a super cute bikini and chasing their child on a crowded beach. I’ve done all of this, and well, I haven’t exactly met anyone.

So, my work-wife, Jemma, took matters into her own hands one evening when she was over and created an online dating profile for me on an undisclosed website. So far, I’ve blocked 43 creepers and have been on 1 date. The date was fun! The guy was cute, older, successful, ambitious and a gentleman. But that doesn’t mean I wasn’t completely wigged out about meeting a complete stranger for a date. I read the headlines about online dates going very wrong—you know, ending in … murder. I’ve also seen Lifetime’s The Craigslist Killer, admittedly more than once (haha). GF killjoy Carlo was less than supportive: “Bad idea. He is going to disappear you. JD is going to be an orphan child and our family is going to be on Dateline’s unsolved mysteries.” Click. Texted him: “You’re an ass.” (I’m smart. Jemma had his name, cell number and the place we were meeting at.)

When *Kevin reached out to me online, I immediately thought he was adorable, hot, WOW. There were many pics of him wearing sharp suits. I eyeballed his profile. We live fairly close to each other and have common interests. We’re both looking for a relationship and not a “casual encounter” — ew. We agreed to meet at a place close to my office and near his apt—it seemed fair. I was very excited leading up to the date, but on the day of the date, I freaked out.

Who is this guy? Do I really want to go on a date with a stranger? I texted Jemma with my concerns. She told me over and over, dating online is like meeting a guy at the grocery store—you have no clue who they are. By the end of our series of texts I was laughing and Jemma agreed to meet me for a drink of liquid courage before my date. That made me feel better.

I slipped into my new (obvi) silky  blue, black and lime green, waisted spaghetti strap dress and a pair of wedges. I shook out my long, mermaid hair and put on minimal makeup, but bright pink lipstick and my Nanny’s antique gold bangle. I felt confident when I kissed JD goodbye and left him with his awesome babysitter. They made this while I was gone. So cool!


Jemma and I shared a glass of wine. And then my date showed up early and Jemma was still there and it was awk, but Jemma quickly chugged her sangria (second glass) and fled. Kevin and I sat at the bar for a bit and chatted. We were both nervous. We moved to a table, ordered more drinks and tapas. The place was romantic and Latin (Read: Sexy). There were twinkly lights and a big open-air space. As we talked more and more, we found a lot of common ground: We’re both Italian. Our parents are divorced. We like the Yanks and the Giants. We’ve been in long relationships that didn’t end well. We want kids. We want to get married. We like the beach. “I’m a beach bum” we said at the EXACT same time. It was cute. We both love NYC, traveling, and good food. After dinner we took a walk. I’ll stop blogging for a moment and let your imaginations go wild. Happy dance.

Then we sat at an outdoor cafe in a garden (hello, awesome) and had espresso.

The night ended. We have another date planned.

I guess online dating isn’t all that bad.

Single parents, how do you meet dates? Are you online?

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More from me: 

Breaking Up Is Hard To Do: The Single Mom Edition 

Who Watches Your Kids When You Go Out?

Single Mom Life: I Danced Till 4 AM and My Kid Got up at 6 AM

Article Posted 4 years Ago
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