Single Mom Survival Guide: Adventures in Dating

I am quickly approaching the two year anniversary of my newly-"re"found singlehood, and feel like I am finally in a place where I can think about dating again. I tackled my relationship fears early on, regrouped on my own, got my life together, and have really embraced being single. There are a lot of aspects of being on my own that I really do enjoy, especially after so many years as a couple. I make my own decisions, I don't rely so much on second opinions, and I can hog the whole bed at night. But at the same time, I am ready for companionship from someone. Someone who makes me laugh. Someone to go to dinner or the movies with. Someone to have grown up conversations with, to travel with, and to let into my life again. I tried my hand at dating early on in the divorce process. It wasn't an effort to find Mr. Right so much as an exercise to see if I still had "it." I was searching for confirmation that, despite my sleepless nights caring for tiny kids and long work days in a poorly lit cubicle hopped up on caffeine and stress, I could still pull myself together, dress myself up, and be capable of attracting the opposite sex. But there is a lot of truth to the idea that you will attract the wrong people when you're not comfortable with being on your own. Most of the people I met were in the same boat as me: recently divorced, bitter, untrusting. Or they were guys just playing the field - something I was never fond of even when I was younger. These dates all went horribly, and I immediately thought it must be me. I was attacting losers, so I must be a loser too. I was embarassed to even talk about these dates, because I thought my friends would think I was nuts. But after a few drinks with friends, these dating horror stories made for good entertainment. And I quickly learned that everyone has been through it, and a bad date (or 10) doesn't make you a bad catch.

So as I embark on this dating adventure again, I reached out to my friends for some funny dating stories from their journeys to find Mr. (and Mrs.!) right. It's always nice to know I'm not alone in this crazy search for love. And as a tribute to those friends that make me laugh every day and remind me that I'm still a hot tamale, I'm sharing some of our most classic dating gems from our archives.

(Disclaimer: Identities have been hidden to protect the innocent, and their stories have been censored to protect the faint of heart. The unrated versions are raunchy and fabulous.)


"I found what I refer to as a solid gold online match: an engineer, who was good looking and seemed nice enough. We met for dinner on a Friday night. He refused to eat, since he made waffle fries at home prior to the date. He also looked nothing like his picture, and in fact resembled the lizard creature from Monsters Inc. He was the most miserable person I've ever met. He told me about his horrible job, which turns out he wasn't in any way an engineer. An hour into the date, he informed me that his mother was there with us at the very same bar. Super! Trying to sneak out wasn't an option, so I spent the next 40 minutes getting acquainted with his mother, who was drunk and high on narcotics, as she recently had back surgery. Between screaming "what's this girl's name again?" and falling off of her bar stool, she did engage me with an unforgettable yet compelling conversation about Chris Daughtry's new album. As my date and I were leaving, he asked to see me again. Umm, were we just in the same air space?!?! No way! Unless of course your mom is coming again."

"I went out on a blind date with a guy right before I was going to be out of town for two weeks on vacation. He made a comment over dinner that it was a shame I was going away, because he had 'needs' that wouldn't be taken care of. At this point in the evening, I was pretty drunk, so I flipped out over chicken fajitas and told him that sleeping with me is a privilege and that he should take care of his own needs."

"I met a guy through a dating website, who seemed like a nice guy trying to make conversation. Like each person on a dating website, I checked out his profile immediately after reading his message. The guy seemed normal, good looking, 5'10" height, great! So we scheduled a date to meet for sushi. Date night arrives and he texts me that he's outside. I jump in his SUV, and we head to my favorite sushi place. As we park and I get out of the car, I look over and couldn't see him after he jumped out. I suddenly see him appear from around the hood of the car and realize that this guy is no where near 5 feet tall, let alone 5'10". Not what I expected, and not a great night to wear platform heels. I looked like a giant!"

"I went on a date with a guy I met through a dating website. He asked me to meet him at a Dunkin Donuts on a Saturday afternoon. He stared at my chest the whole time and proceeded to tell me he was waiting for his new teeth to come in, since his actual teeth were broken in a car accident. He then segued into conversation about his grandmother, who keeps asking him when he is going to get married and settle down. He says, 'I just haven't found the right girl, but maybe I won't have to look any further.' We then head to the movies, and the only movie playing was the kids' Disney movie, 'Up.' We were the first ones in the theater, so he tries to make out with me. I stop him just before the theater starts to fill up with little kids and their parents. After the date, I say thank you for the nice time but that I didn't feel any connection. So he asks if I like German guys because he has a German friend who just recently broke up with his girlfriend that tried to stab him. I wasn't really sure how to nicely respond to that."

"New to world of attempting to date while in my 30s, and after serious pressure from my friends, I thought 'what the hell' and put myself back out there. I was in my early 30s, divorced, good career, attractive, and slightly athletic, I should be a catch! One evening, I met a very attractive woman in her late 20s for drinks at a local bar. I pull up nervously to the bar and wait outside. Within minutes, a HUGE diesel pickup truck pulls up and my lovely 'lady' emerges. We exchange awkward hellos and went in to get a drink. After the introductions and first round was purchased, she immediately withdrew her phone and began texting. Minutes drug by and I chugged my beer as fast as possible. After what seemed like an eternity, we finally began the horribly awkward conversation. As she loosened up, she told me the story of her long-time ex boyfriend who now resides in federal prison convicted of embezzlement (and showed me the article online to prove it). She bragged about how awesome that relationship was because he bought her a house 30 minutes away and let her do whatever and whomever she pleased as long as she was ready for him when he needed her. Wow. At this point, I ordered another drink. Not because I had ANY interest in this shallow, monster truck driving 'lady,' but because it was just far too entertaining to leave. Over the course of the next 2 hours, she told stories of a myriad of other awful situations. Finally, the booze began getting the better of her and she really came to life. She began making fun of EVERYONE in the bar, LOUDLY. And I don't mean the light jabs about this fella's mullet or that girl squeezing into yoga pants - I mean rude, cruel, awful things about everyone's appearance, clothing, demeanor, laughs, voices, race, you name it. I was mortified because people were beginning to look at us, and I was even quite sad for this horribly vane, disgusting excuse for a human being. I quickly looked at my phone and excused myself."

Putting yourself out there is an adventure in itself. You definitely have to kiss a few frogs before you find your prince or princess the second time around. I'm looking forward to the challenge - I'm definitely a handful, so I'm sure I have been the topic of someone's nightmare dating story at a bar somewhere. If nothing else, these frog tales make for great happy hour conversation, so I always look forward to drinks with friends. I wish you the best on your post-divorce dating adventure!