The Bachelorette’s Jeff Talks Bentley & Wearing the Mask

Courtesy: ABC/Rick Rowell

We are only three weeks into The Bachelorette and there has already been more drama than in some past seasons altogether. The first night, Ashley Hebert sent Tim home for drinking excessively, she ended up with a bachelor who wore a Zorro mask, William, one of her favorites, made her cry by hitting her vulnerable spot last week at the roast, and then in the last two weeks, there has been the heartbreak of Bentley.

Ashley was so distraught after Bentley decided to leave the show that she canceled the cocktail party, leaving Jeff Medolla, the bachelor in the mask, with no opportunity to talk to her, so she selected him to go home. For some reason the charm and mystery that is Zorro didn’t translate to Jeff.

Now, we talk to the ousted bachelor about his reason for wearing the mask, his take on Bentley and if he was really on The Bachelorette to find love.

What did you the other bachelors think of Bentley while you were taping, and what do you think of him now that you’ve gotten to see the show and what he said?

Jeff Medolla:  Bentley was my roommate.  I hung out with Bentley a lot and I don’t know.  It’s kind of a hard read, to be honest with you.  I’ve been in sales and whatnot my whole career, and I’m a pretty good judge of character and can read people very well.  And my situation walking into that house was basically like a social experiment. I knew what I was getting into.

I knew I was going to walk in and get [flayed] immediately by pretty much everybody.  But there was an exception of a few people in there that did not immediately shun me, so to speak, and Bentley was one of them. Immediately I was talking to Bentley and Ames.  And so those two guys right off the bat were really cool.  And I knew what I was doing from the get-go.

Now that I’ve seen some of the stuff, I know he wasn’t really happy to be there.  I don’t know, it’s kind of confusing, to be honest with you. I just think Bentley’s demeanor is … Bentley, he seemed very just like disinterested.  Kind of how he was, I guess.

At what point, after being cast on the show, did you decide that you were going to wear the mask and why?

Jeff Medolla: Good question.  So people that know me, my friends and family, know I’ve got an extremely dry sense of humor, and I love comedy.  I am a businessman and I own a wine called Freaky Muscato, and I’m a huge risk taker.  I knew I wanted to walk into that house, because there’s been 600-plus people that have done this show before, and I was: Why the hell would I walk in as just regular old Jeff?  I mean that’s just easy.

So I was thinking about maybe doing like a big, fake mustache, you know,  like Tom Selleck or something, and maybe I was going to get out of the limo eating a donut, and I thought about being a fake limo driver with a hat and gloves, and really kind of flipping the script around and really throwing her off and throwing everyone off.  And that’s how I operate.  I knew I wanted to go in disguise, and that’s kind of how I had the mask idea. After talking to the producers, of course, they were like, “I think it’s genius,” and, “let’s roll with it,” so that’s what I did.

As much as it was a joke, there was great meaning behind it because there is a great message, which is: Don’t judge me for what I look like, or maybe money that I have or materialistic things.  And how hilarious would it be to walk into this frickin’ mansion with a mascot?  I mean who in the hell would do something like that?  But, for me, hey, I had a brain hemorrhage when I was 29 years old.  You only live once, and I’ve pretty much said, “That’s it.  I’m just going to do it.  Why not?”   And that’s why I did it.

What if you could have a do-over.  After watching how it went down and that Ashley said, “Oh, my God.  He’s older than I thought.”  And then you told her about your illness.  Do you think that you would do it differently this time?

Jeff Medolla: No, actually, I don’t, because I think that the three oldest guys were myself, 35, that Tim guy, the first night, he’s 35, and then I know J.P. is like 34. What’s funny is, I get people that tell me every day that I look really young for my age. I mean I run six miles every day,  so I don’t know.  I guess I don’t think I look old for my age or anything like that.

But to answer your question, no, I don’t think I would do it differently.  It’s just one of those things where I knew that no matter how I was shown on the show or the what perception of me was, , whether it’s weird, strange, odd, well, yes.  I’ve got a company called Freaky.  And I sell wine that’s called Freaky.  And it’s just there was so much meaning behind it, and that’s why I probably wouldn’t change it, no.

Were you actually there to try and find love and have a relationship, or were you there to make a point?

Jeff Medolla: Well, I could tell you that if you spoke to any of the casting directors about me, they would tell you that I’m a very genuine, sincere person, and I do want to find somebody that I can spend my life with. I’ve had great relationships with people, and, you know, what’s hilarious about this whole thing is that I am a very normal, regular person.

And yes, to answer your question, I do.  But you don’t go there knowing exactly who it’s going to be.  If you get lucky and you walk in and there’s like chemistry or something, then it makes the experience that much better.  But again, I didn’t talk to Ashley all that much. I only talked to her like three times like in the whole time that I was there.

The Bachelorette returns tonight at 8 p.m. on ABC.

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