My first job out of college was doing in-house marketing for a plastic surgeons’ office. While the job sucked (they wouldn’t let me run any ads with the phrase “tig ol’ biddies” in them) and the pay was slightly below what I made as a tutor in high school, the benefits were amazing. Not the medical insurance offered or accrued vacation days, but the sheer amount of gorgeous girls I worked with. This company was 90 percent women and they were without a doubt hired for their looks and not their actual skill. Being a 22-year-old male with no scruples and a talent for ill-advised hookups, I (of course) took full advantage of my work situation, HR be damned.
About six months into me working there, I walked into the office and immediately noticed that there was a new Medical Assistant who had just started. I, being a gentleman and a good coworker, immediately introduced myself and ended up inviting her out to grab a drink with me after work. We hit it off over some whiskey sours, and soon enough found ourselves back in my bed, laughing about what a bad idea this was. Total elapsed time between her starting her first day of work sleeping with me: 16 hours.
As we were getting ready the next morning, I grabbed what I thought was my phone to check the time. But upon seeing the background, immediately turned to her.
“So, who’s this kid that’s your background? A little cousin or a kid you babysit?” I asked obliviously. “Uhhh, no, that’s my son,” she answered tentatively, “I had him when I was eighteen.” I was floored. I had never managed to cross “MILF” off my sex bucket list, but bragging rights was the furthest thing from my mind right then. I had slept with a coworker who had a kid. I was fucked on so many levels. I could barely take care of myself, how could I possibly have a relationship (casual or not) with someone who was responsible for a tiny human’s life? My brain told me to cut and run, but my dick, who is much more persuasive, told me to continue things with this girl and see how it went. We ended up casually dating for the next several months, and although it was unlike any relationship I had been in before, there were definite pros and cons.
Pro: She’s straightforward about what she wants. Moms have too much going on to play a long game of “What is this relationship?” Most girls in my past had been game to hook up for weeks and even months, all while suppressing their desire to define the relationship, so as not to ruin their persona of “the chill girl.” This chick asked me what my intentions were the second time I hung out with her. When I answered with an honest desire to keep things pretty casual, she told me she understood and was also fine with that, but if she developed feelings, she would end things. That kind of honesty was refreshing for a guy with three high school/college relationships under his belt and it removed nearly all drama from the relationship.
Con: Her time very is limited. She’s got a kid that needs to be picked up from school, watched at all times, and cared for. This girl’s son actually had Autism, so any option for a nanny was very limited to someone with proper certification, not just a friend or cheap sitter. This meant that the only time I could see her outside of work was when the kid was with his father, which due to that guy being a scumbag, was not very often. When you’re first dating someone, it’s hard to suppress the desire to be with them all the time, and it’s hard to further a relationship when quality time together only happens every couple weeks.
Pro: If you’re sick, she’s the best person to have caring for you. It’s a scientific fact that kids, as a result of putting everything within arm’s reach in their mouth, are sniffling germ bundles for the first four years of their lives. Because of this, moms get a ton of training on dealing with whining crying babies, which is 100 percent what I turn into when I get sick. Need someone to rub your back and give you medicine when you’re so sick even the softest blanket hurts you? Date a mom. Need someone who isn’t going to roll their eyes at you when you ask them to get you a glass of water and Alka-Seltzer for the 11th time? Date a mom. Also, if possible, date a mom who has medical training and access to prescription drugs. I’m not saying she grabbed some for me, but I will say the flu season of 2015 was my easiest one yet.
Con: You’ve had drastically different life experiences. While I was moving into my frat house, eyes wide at the sight of young “adults” Consuming Beers In The Dumbest Possible Ways and shamelessly hitting on every girl within a 100-foot radius, this girl was reading “What To Expect When You’re Expecting.” When I took years off my life watching Porter Robinson at spring break Lake Havasu, she was teaching her son how to walk and researching pre-schools for him. A big part of dating is sharing stories and experiences with each other (so I’ve heard), so there is going to be some disconnect there. When she’s talking about how she had to deal with explaining her divorce to her son and how proud she was when he said his first words, you’re going to feel out of your depth. When you tell her the funny story about that time your friend got a black eye because the stripper pole in the house basement wasn’t properly bolted to the ceiling, she’s going to assume (rightfully), that you haven’t led a very impactful life.
Pro: She has her life together (and that will make you grow). Being a parent is like taking a crash course in responsibility. Gone are the days of doing whatever she wants, because now she’s responsible for a whole other person’s life and wellbeing. When your main concerns are how your team is going to through this round of the playoffs without your star player and whether you can afford to do New Orleans bachelor party if you pregame a little extra for the next month, she’s got a little more on her plate. Proper diet, exercise, social life, school, extracurricular activities, and play dates. These are just a fraction of the things moms have to deal with on a daily basis for their kid. Unless you are a total piece, some of this will rub off on you. I’m not saying you’ll immediately quit drinking, sign up for a marathon, and get a promotion, but being around someone who handles way more than you do and does it well is going to motivate you to grow up a little.
Con: The relationship will have to become serious quickly or end. After about three months of casually hooking up and going on dates, this girl told me that she was getting more serious feelings and that if I wasn’t prepared to be in a serious relationship, we would need to end things. I elected to end things, but if I hadn’t, she told me she would have had me meet her kid and see how we got along. When dating a mom, there is a lot less time to “feel each other out,” and slowly build up to a serious relationship. When there is already a kid in the mix, a serious relationship is going to involve parental duties and becoming part of a family, not just committing to a girlfriend. If you can’t see yourself being a dad and having a family, you absolutely cannot be a shitbag and keep the relationship going just because you like the girl. Your feelings are not as important as the feelings of this child, who already is dealing with two parents who aren’t together. Considering my only big responsibility in my life was a beta fish I kept in an empty Bacardi bottle and routinely forgot to feed, I was nowhere near ready to make any further commitment to her or her child.
All in all, I was (and still am) not ready to be a father. However, I’d like to think dating a mom helped me grow as a person and brought more clarity to my future relationships. At the very least, hearing her talk about staying up all night with her kid has gotten me better at remembering to use condoms. .
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