Should I Date This Guy Who's 18 Years Older Than Me -- With Kids?

Has anyone dated a man old enough to be your young dad?
Publish date:
May 10, 2013
Dating, age, older men, help me

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I’ve been weighing some pros and cons lately. I know this may come as a shock to some of you, but a lot of how I conduct myself on xoJane isn’t exactly how I roll in real life. In fact, I’m actually really private and have a hard time really delving into the personal details of my life, as well as going public with my politics. I like that here I can pick and choose what I want to share and what I want to hide.

However, I have noticed you guys have no problem sharing your opinions so I thought who better to come to about my current life dilemma than xoJane commenters. My mom, you ask? Nope. I choose you.

Anyway. So Mandy said she wanted me to meet her producer friend for “business reasons,” but pretty soon I realized that Mandy was full of lies and she was actually trying to play matchmaker because she can’t stay out of my love life. I suppose she thinks I need to be dating older guys instead of the post-frat douchebags I keep telling her about. (My taste in guys is notoriously the worst amongst my friends. I know, I know.)

“Fine, Mandy. I’ll talk to him, but if he’s fat, bald with fucked up teeth, you can forget it. I don’t care how many bags of money he has,” I told her.

The thing is, although I have daddy issues just like every other dysfunctional commitment-phobe, they have never presented themselves in the form of being attracted to older men. I actually never understood the appeal. I’ve always preferred guys my own age, usually plus or minus 2 years. Most older men I have met, whether they expressed interest or not, usually spoke in such a condescending manner to me that instead of putting them in their place or trying to prove to them that I’m not as dumb as I look, I just walked away.

Take your mansplaining down the street, pal. I’m not interested.

So when I finally got to talk to Scott Einziger, I already had my guard up. What’s this old guy have to offer me and is he going to treat me like some wide-eyed 21-year-old wannabe actress from farm country just trying to make it in the entertainment business and see her face on the silver screen?

Well, the first thing I noticed is that my perception of what a 46-year-old single dad looks like couldn’t have been more off base. (I told him I wanted to do this article, and Scott gave me the OK. Maybe because he worked for Howard Stern for 10 years. I guess he has a pretty thick skin. He even said I could show his picture.)

“I honestly don’t normally date much younger women,” Scott said when we finally connected by phone (he lives in Los Angeles, which I suppose is another obstacle, but I’m trying to keep an open mind).

“And I’m not sure if I would date someone who’s 45 with two kids,” I said. “So I guess we already have our hesitancy about this set-up in common.”

We both laughed, because if there’s one thing we can bond over it’s the fact that we have one very pushy albeit well-intentioned friend in common: Mandy.

“I’m trying to be more open-minded to set-ups,” Scott said. “I also have always been curious to date a writer. You seem pretty fearless and don’t care what people think of you.”

I do like a guy who knows how to compliment me -– and doesn’t do it in a dumb way where he just focuses on cheesy superficial things, but seems to actually sense who I am as a person.

Since he asked about my work, I asked about his. I had done some Googling and was kind of intimidated. He made it in the entertainment industry as a reality TV producer. He worked for Stern for a decade. He’s one of the guys behind "The Amazing Race" and "Big Brother." He’s won an Emmy. Dude comes with credentials. I mean, that’s definitely where older men have younger guys beat: career establishment.

“I don’t want to be on reality TV or anything like that, so you know,” I told him, since I figured he probably had people bother him about that all the time.

“Good, we have that in common, too,” he said. “In the last few years, I’ve transitioned into movies.”

We had a really great chat, but I’m still a little hesitant if I want to take on all the baggage that a twice-divorced dad with two kids comes with. Not to mention our age difference is one of a legal adult. This is serious stuff to think about!

First off, what I really loved is how passionate he is about his work. He told me though that his dream was always to transition into movies, so, while feeling down on himself after his last divorce 2 years ago, he thought he’d just give it a go. He started his own independent film production company Unguarded Content.

This all a big pro for me. I think it’s really attractive when a guy actually loves what he does. I go out with far too many finance and lawyer types who are only in it for the money. They are just as miserable in life as they are in their work.

We’re both looking for someone to have your back 100 percent and that’s something that didn’t happen with his wife. That didn’t happen with my ex, either and the break-up made me realize that that’s what is the most important thing to me in a future boyfriend.

We both really like Don Julio tequila. We do have some things in common.

Another pro is that he’s nuts about his kids. From the pictures he showed me (he showed me like a dozen, of course) they are adorable and super sweet.

This is all well and good, but I’m 28 and the only thing I can bring myself to mother is my cat. I know I want a kid or two down the line but do I want someone else’s kids? And let’s say we hit it off, will he want to have more kids? What if his kids hate me? What if his ex wife hates me and doesn’t want me anywhere near them? I know this is all too soon, but with guys my age, these are not questions that come up because they are not applicable.

Finally, this will never fly with my mother. I was hanging out with a guy 10 years my senior a few years ago, very casual, but I mentioned it to my mom in passing and suddenly there was a pause. She then said “Oh, honey, after 35 they just start falling apart. I don’t know. You want someone your own age: you grow together, you become established together. There’s a bond.” She then went on to talk about how older men who like younger pretty women will always like younger pretty women, but I won’t be young and pretty forever.

No matter how attractive, established and caring this guy is, my mother would have none of it. I’m a Russian-Jewish immigrant; my mother’s opinion means everything to me.

He told me that even though he’s enjoyed being able to finally date (he married his first wife young and divorced her two years later, he and his second wife were together for 15 years), he’s now pretty tired of it. We both called it “dating fatigue.”

So, bottom line is we both like each other … so far … and there’s no pressure, which I like because I hate feeling pressured. But I need some advice on how to go about this. Has anyone dated a man old enough to be your young dad? What about dating someone who already comes with kids? I’ve never done either of those things before. Please advise.