12 Dating Nightmares That Can Only Happen to Moms

Wendy Robinson | Aug 29, 2016 Love & Sex

Back in the day, it used to take me HOURS to get ready for a date. There was choosing the right outfit, calling my friends on the phone to confirm my outfit choice, doing my hair and makeup until every last lash was just perfect. I thought dating was complicated back then. I really can't imagine doing it now!

This is both because I'm happily married (so the whole dating thing is frowned upon) and because I have kids. I barely have time to shave my legs, let alone get prepped to look cute for a night on the town. 

But I do have some friends who are entering the dating world again as single moms after divorces and I am so rooting for them to find love again. 

The path to love, though -- especially for a dating mom -- can be rocky. Read on for some totally awkward dating moments that could only happen to a mom (#11? SO CREEPY!).


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  • The Very Short Date

    Image via iStock.com/gremlin

    "I connected with a guy online and was super excited to finally meet him in person. We set up a coffee date because we both have crazy schedules. I had a babysitter for exactly two hours. Hard deadline because she had to go to school. 

    Well, I went to the coffee shop and waited and waited and waited. It turns out that he went to the wrong coffee shop first and then got stuck in traffic. By the time he showed up, I had 15 minutes left on the babysitting clock. He was cute and funny and I had to bolt like Cinderella. Such a bummer. He never called me again." -- Christy J., Glendale, California 

  • Big Bear? Big No!

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    "I had gone on one date with a guy and it was okay. No major chemistry but nice enough to go for a second date. I guess I mentioned on date #1 that my daughter's birthday was coming up. He showed up for date #2 with a five-foot-tall teddy bear as a gift for her! NO! Too soon. It creeped me out. We never went out again but she still loves that damn bear." -- Jessica B., Indianapolis, Indiana 

  • Pee Problem

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    "I got set up with a cute younger guy. He thought it would be fun to go to one of those indoor trampoline places for a date. It is fun -- if you haven't had two 10-pound babies! I totally peed my pants. It was so embarrassing." -- Name withheld by request

    More from CafeMom: 10 Single Moms Share Their Biggest Relationship Deal-Breakers

  • No Naked Pics!

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    "I had a guy who I was chatting with on a dating site send me a sexy picture -- unsolicited. And it came through when my kid was playing on my phone! YIKES! Don't send a mom a clothing-optional picture unless she asks, okay, dudes? I don't want to have to explain THAT to my toddler." -- Mari C., Roswell, New Mexico

  • Party of Three

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    "My babysitter bailed at the last minute so I ended up having a first date with my 5-year-old along for the ride. I should have just canceled. It is hard to flirt when your kid is making a mess at the table and challenging your date to a burping contest." -- Alex K., Costa Mesa, California 

  • Go Time

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    "I was starting to get serious enough with a guy that I agreed to let him pick me up at my house so he could meet my 7-year-old son. Well, they met. And started bonding over Pokemon Go. And ended up walking around the block together trying to catch a whatever and leaving me behind! Dumped for my kid!

    We did end up going out later, just the two of us, but I still have to laugh that they just left me standing there." -- Rachel V., Des Moines, Iowa

    More from CafeMom: 12 Nightmare Dating Texts That Make Life With a Cat Sound OK

  • Plane Story

    Image via iStock.com/Radist

    "Oh -- I know my worst story! I went on a first date with a guy who'd just gotten back from a trip for work or something. Anyway, apparently he was seated next to a mom and baby. He spent literally 15 minutes talking about how awful it is to sit next to kids on a plane and how the kid was 'a brat' for crying and that the mom 'didn't shut him up.' 

    Um, no. I've been that mom, jackass. I am not here for a guy who is all about trashing a parent. I left before dessert." -- Kari S., Wheaton, Illinois

  • The Interrupter

    Image via iStock.com/matka_Wariatka

    "I had a GREAT first date. He walked me home and we were doing the whole kissing-goodnight-at-the-doorway thing when I heard a knocking at the window. It was my 4-year-old, staring at us. Apparently the babysitter let him stay up until I got home. At 11 p.m. Awesome. Super romantic way to end the night." -- Laura W., Saint Paul, Minnesota

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  • Too Soon

    Image via iStock.com/Solovyova

    "When it comes to dating me, there is a fine line. I need you to be okay with the fact that I have kids, but not like TOO into the idea of it, if that makes sense. Like, there was a guy who just wanted the instant family thing. He asked if he could help teach my son to ride his bike. On the second date. Too soon, dude." -- Melanie N., Dallas, Texas

  • The Creep

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    "I'm a single mom who got pregnant via sperm donation, so I dated off and on while I was pregnant and then started dating again when my baby was 6 months old. I realize that is kind of weird for some guys, so I'm always upfront about my situation. 

    I might have been too upfront because I ended up getting asked out by the guy who spent the whole date wanting to talk about breastfeeding. I left when he asked if he could 'get a taste' and then said he was jealous of my baby. Ewww." -- Dina T., Minneapolis, Minnesota 

  • The Awkward Intro

    Image via iStock.com/andresr

    "I usually only go out on dates when my kids are with their dad. I'm taking things super slow when it comes to my kids' knowing that I'm dating. 

    One night I was scheduled to go out with a guy I've been seeing for a month or so. I planned to have him come over for dinner once the kids were with my ex. Well, of course this is the one time my ex is running late so he and my date arrived at the same time. It was so awkward. The kids were excited to see their dad but didn't get why this other guy was there. My date felt awkward. It was the worst." -- Michelle P., Tucson, Arizona 

  • Too Much in Common

    Image via iStock.com/AzmanL

    "I went on a date with a single dad. He was cute and nice and we bonded over being a single parent. We bonded too much over that, actually. We ended up spending the whole date talking about our kids. Not very romantic at all. We ended up doing a playdate for the kids but we never went out again." -- Sarai E., Saint Paul, Minnesota 

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