Sex Advice From Modern-Day Mad Men

By Maura Hehir

Prolonged contract negotiations over at AMC mean we're suffering an unusually long wait for the next season of Mad Men. To help tide you over, we asked real-life ad men how their love lives compare to the TV version.

Nick, 25

What gives ad men an advantage in the dating arena?
Mad Men does, because it makes people think you're way cooler than you are. I mean, it's a cool job — advertising itself is a very American thing. It's more interesting than finance; it's something that a lot of people want to talk about, as far as talking about work goes. And as creatives, we're kind of used to thinking snappily on our feet and being witty.

What would you say to ask someone out on a date?
Every situation is unique. I usually try to make it kind of personal — I'll comment on something they're wearing, or the way they look. Strike up a conversation about something that's happening. I don't really use pickup lines, because who uses pickup lines?

Do ad men still have as much sex as they apparently used to?
I guess so. I only got halfway through the first season of Mad Men.

You're a bad ad man.
I'm a bad ad man. I've dated three girls who I work with. And I'm not too unique in that. One of my close co-workers recently started something else up with another co-worker. I mean, there are a lot of young people at my agency, and we all get along really well, so it's kind of easy for that kind of thing to happen. So yeah, we're all pretty — I don't want to say promiscuous, but sexual, definitely.

We've seen Pete Campbell, Don Draper, Roger Sterling, and Duck Phillips all get freaky on Mad Men. Who are you most like?
Pete is the weird creepy account guy, right? Okay, we can get rid of him. I know Don. Roger Sterling has the white hair. I don't know Duck. From my limited experience, Don Draper's whole "I'm not who I say I am thing" might be a little bit weird. At least with Sterling, you know what you're going to get. I'm kind of more like that. I'm not really very mysterious — I am what I am. 

Your job is about convincing people to want things. How does that translate to your dating and sex life?
I wasn't trained as an advertiser — I was an English major. I worked in politics before. So advertising is my job now, but to me, sex and dating is more something that I want. Not to sound too sappy or anything, but the best is when two people agree that they both want something. In advertising, part of being a good salesperson is knowing what the other person is like, what they need and want, and how to tailor yourself to that. I don't think I do that in dating. I'd rather have a more genuine connection, as opposed to constantly trying to sell. There are so many people. I don't feel the need to convince the one person who happens to be talking to me at that time that I'm the best option. I'm not getting paid for it.

Over the summer, I started having sex with one of my best friends. We both have feelings for each other now, but I don't want to be in a serious relationship. I also don't want to stop having sex with her. What should I do?
You kind of know the end of the story already. I met somebody at work. We hit it off as friends immediately, and we ended up starting to date. But once you cross that threshold, it's kind of impossible to get the friendship back. It ended kind of badly. We had built up a friendship, and that friendship meant a lot to both of us. She's moved on — she's living with somebody else now. This was like a year ago. But she recently contacted me to say, "One of the things that I hate most about what happened to us is that we lost the friendship." I don't know of any successful stories where people have remained friends and were actually serious lovers at one point. So good luck.

I have a lot of male friends and I value their friendships a lot. But recently, it seems like they always want more, and I never pick up on it until someone else tells me. How can I stay friends with them without coming off as a tease?
I'm guessing whoever wrote that is pretty attractive. It's hard. I've been on both sides of that. I think the best thing you can do is just be clear. You know, if you're being too flirty, this is something that's going to keep happening. You have to be aware of your own level of attractiveness, and try to kind of keep it in the holster when you're around your friends.