Dylan Reiff: Mystery "trying to find his harem of low-self-esteem club rats"

Dylan on VH1, before his transformation
Dylan on VH1, before his transformation

This week's cover story focuses on Twin Cities pickup artists, many of whom were inspired by VH1's The Pickup Artist. Turns out, one of Minneapolis's own appeared on the program.

Dylan Reiff, a 28-year-old who grew up in Golden Valley, showed up as part of the final challenge in season one. He played a hapless geek that one of the final contestants had to makeover in order to win.

City Pages talked to Reiff about pickup, Mystery, and the state of modern dating.

How did you end up on The Pickup Artist in the first place?

I had recently moved to Chicago, and I was still acting in those days. I originally went in for the interview, and they liked me. Basically, I was trying to magnify the traits that they were looking for: kind of be over the top, nerdy, wacky, and funny. I tried to present myself as un-dateable, without losing endearing qualities.

What did you learn about pickup from the experience?

I learned that it was real. These are people who use a very calculated strategy. They know who their target is. They know only to go to clubs that have a very particular type--that this has a higher success rate. But a lot of it is bullshit. It is this force, and there's a dark way to use it and a light way to use it. There are ways to use it that I think are reprehensible.

Dylan after his makeover on "The Pickup Artist"
Dylan after his makeover on "The Pickup Artist"
courtesy Dylan Reiff

What did you think of Mystery?

He's trying to find his harem of low-self-esteem club rats, and he likes that power. I think it does work. He probably does sleep with a lot of women. But I think that he's a genuinely sad person. I think he probably spends as much time having sex as he does crying. And probably often at the same time.

What did you think of Kosmo, who ultimately won the show?

Kosmo was a dick. From the second I met him, it was really clear that he was an actor. It was really clear that he didn't have any problems picking up women. His shtick was that he was really shy, and that he had trouble closing down around women. After meeting him, after two seconds, I could tell that it was just not true.

What did you think of the makeover they gave you?

I really did end up looking like Super Producer J.R. Rotem. Overall, corduroy blazer with Grateful Dead skeletons on the inner lining, not really my type of swag. I swag to a different drummer.

Was there anything you learned on the show that you've applied in your own life?

I think how they talk about confidence was actually a redeemable. You can't put yourself down all the time. I would do a lot of self-deprecating humor, but I think that does come off pretty unattractive on a date.

Dylan, sans his Mystery makeover, with the girlfriend he found without the help of pickup
Dylan, sans his Mystery makeover, with the girlfriend he found without the help of pickup
courtesy Dylan Reiff

You seem pretty cynical about pickup. Why?

We have a dominant "bro" culture that I think ties in with our culture of date rape. We've moved from a culture of consent to a place that is really dark. We almost gave a Vince Lombardi trophy to a serial rapist, and no one would have batted their eyes about it. I think that the combination of where we're at as a culture with alcohol and consent has created a very weird place.

What's your favorite memory from being on the show?

I guess the most shocking thing is that I was only onscreen probably for 10 minutes, and I was recognized for two years. That was the most interesting thing about the experience: to see how deep that show connected with America.

Do you have a girlfriend?

I do. She's wonderful. And she's going to love reading this.

Check out Dylan's appearance on The Pickup Artist below:

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