I dated a DILF so hard and learned a few things in the process

I dated a DILF so hard and learned a few things in the process

SexSeptember 28, 2016 By Lily Roosevelt

The dating world for post-grad 20-somethings is a crapshoot. Not only is every type of human available to you, but also, you’re out of college and age has suddenly become just a number. Under these circumstances, any fantasy can be fulfilled — especially the DILF fantasy.

Who wouldn’t jump at the chance to jump a silver fox? So, you take the plunge and get involved with someone over 30 … with a kid. Why not? You’ve got a college degree, I mean … you’re a grown ass adult.

After all, there are major advantageous to dating an older man. You’ll never have to worry about playing games. He’s aware of his own mortality, so he’s direct. He’s experienced enough to know what he wants.

Dating is a blast. This is partially due to his grown-up bank account, but partially because he’s had 10 or so years when you didn’t even exist to come up with great date ideas. Going out on the town with him is seamless. He expects you to order well and make good (expensive) choices. You’ll want the date to last all night, and it will. He will woo you hard.

Speaking of that 10 years he’s had on you: during that time, he’s had many, many women to teach him the wise ways of pleasure. And you’re not even jealous. You know he’s only got eyes for you. The security and lack of games allows you to be the perfect pupil and receive all the tantalizing tactics of his great lovers past. He is persistent and patient.

And when you fight? Go ahead, throw a tantrum, his 6-year-old does that all the time. Your fit won’t even compare to what his ex-wife used to do. And, as the father of that same 6-year-old girl, he will be nothing but the perfect example of a gentleman. 

But once the princely magic starts to wear off, the reality of the kid will set in.

Ah, the kid.

A lot of things change in your life because of the kid. It’s really fun to get high and then go play with kids, but soon you get the feeling you’re not “allowed” to smoke pot anymore. Or maybe your DILF, being the direct gentleman he his, will flat-out address the issue and say, “You aren’t allowed to smoke pot and be in my child’s life.” That’s when you begin to understand what you are committing to. Are you really ready to give up your relationship with Mary Jane for some else’s child?

Suddenly, what you start to learn is that DILF = Baggage. Everyone in the world has baggage, yes, but those who belong to the DILF category have very visible, towable baggage, namingly, a child and an ex.

The doorbell announces his past relationship every Sunday at 10 when “mom” comes by to do the drop. You realize that the truth is, their relationship will never be “past.” At best, you could be integrated into their relationship as some kind of weird nanny/dad’s sex “friend,” but that won’t happen until everyone is ready for you two to get serious.

And when “mom” isn’t peeking around corners, you can sure bet little Bobby or Sally is. Careful riding your new stead, because the kiddo is just a wall away and scared of the dark. Chances are she’s about to sulk into the sheets, and you’ll be bucked off into the crack between the bed and the wall.

As the light of the morning drags you out of the crevice, you realize you can’t be his number one.

You might be an equal — if you skipped your birth control for a week and added your own little minion into the mix. Maybe that is what he expects you to do? The stakes are higher with a dude who feels more mortal every day.

There isn’t any room for daydreaming about the tiling and granite counter tops in house you’ll eventually buy together. He already has the mortgage. He already has the kid. He’s just looking for the missing piece … a wife. In his eyes, it’s time to gear up, dawn the apron and start scheduling family meals around soccer practices.

If this isn’t where you saw yourself three years out of college then best cut the cord quick.

Leave them to a waning 29-year-old. She’ll save them and herself too. You’ll be free to get on with your 24-year-old dreams of bagging that almost famous contemporary artist that only has to wait tables twice a week. Because when capital "R" in reality sets in, that hard charging, communicative man that you prayed for when faced with juvenile douchebags, is actually the strongest deterrent for a committed relationship around. Dads and their ex-wives might get you running back to casual sex and nameless one night stands in no time.