Credit: Rick Rowell/ABC Television Group © 2011 Disney Photo: Ashley Chats With Jeff in The Bachelorette Season 7, Episode 3

Did you learn any secrets about the guys or something that surprised you about them?
No, not really. I guess, I mean, a lot of people are fairly surprised at the things that Bentley was doing in the one-on-ones and stuff like that. I think, my thing is I’m a former hockey player, OK. Talking sh*t is part of the game. What good does it do to talk sh*t when you go back to the locker room? Nothing. So, me, if I’m going to talk sh*t when I play hockey, I’m going to talk sh*t to somebody’s face… Certain people play the game and whatnot, but you see old contestants that have been on the show who are outspoken and whatnot, you give credit to those people because they’ll talk sh*t to your face… I think it’s easy to go talk sh*t behind your back, you know, in front of the camera, behind everyone’s back and stuff like that. I mean, I didn’t talk sh*t about anybody while I was there. I was just like, you know what, it is what it is. They don’t have any footage of me ever saying anything negative about anybody.

What are you going to do with the mask? Are you going to auction off for charity, put it in the Bachelor museum?
I had two of them… I don’t know what I’m going to do with it. It’s a good question, though, ‘cause I’ve had hundreds of people saying “Are you going to start selling masks?” And I’m like “I don’t know, maybe I will.”

Were you blindsided when you saw the things Bentley said to the cameras, especially when he called you guys idiots for believing him?
I think he is a tough read, but I don’t know man. I had some pretty deep talks with that dude and I’m sorry, there is absolutely no way that I don’t think he was missing his daughter. I think he missed his daughter. I mean, I’m not kidding you. Him and I, we roomed together and we hung out a lot. He doesn’t drink alcohol. I don’t drink alcohol. I don’t drink alcohol, not because of religion, it’s just because I’m big into my health and, like I said, I run a lot. I mean, don’t get me wrong, occasionally I’ll have a glass of wine, and here I sell wine … I’m just not big into drinking. He and I seemed like we had a lot of things in common. I don’t know, I think it might just be like he might’ve got a little loose-lipped in some of those one-on-ones. I don’t know. For me, I think it would’ve been easy just for me to — I had a freakin’ mask on, for Christ’s sake. I could’ve easily been in there and been like “Screw all these tools, I don’t need this bullsh*t.” I could’ve sat there and been like “I’ll whoop all these dudes asses,” or something. But I didn’t do that because it’s just pointless. It’s easy to go do that. That’s the easy thing. I don’t know. I’m confused a little bit on it, yet again it’s like ratings and TV and I don’t know.

Who is the right guy for Ashley and, in your opinion, do you think she’ll end up engaged?
I don’t know, I think maybe she’ll end up engaged. It’s hard to say. I think that, I could tell that there were a few guys that really seemed sincerely into her. One, of course, everybody’s kind of talked about, JP. JP seemed like a nice guy. I didn’t talk to him a bunch. Again, the reception to me was never real warm. So it wasn’t like — you know, a bunch of dudes over there talking, I’d come over, I’d have to really engage in the conversation you know and try really hard. I’ve never had to do that. Some of my best friends are African-American, you know, I get along with everyone. But to answer your initial question, probably like JP — JP seemed like he was genuinely into her, so I’d go with him.

Were you hurt or upset by the things Bentley said? He talked a lot of sh*t about everybody. Do you think he’ll have a hard time finding a girlfriend after this?
Unfortunately, we live in a country where scandalous sh*t sells and nice guys are kind of like “Eh,” then all of a sudden you’ve got an a**hole dude and all of a sudden that’s what totally sells. I don’t think Bentley’s going to have any problem with any girls, to be honest with you. Just because it seems like a lot of girls like a**hole guys. I don’t think Bentley is, like, a total a**hole, I just think he was playing the camera and doing whatever. I don’t think he really wanted to be there, after maybe four or five days I could just tell. Again, I can sit here and admit I didn’t totally — I mean, my whole situation was very unique, too, ‘cause again with the mask I was kind of getting to the point where I’m like “Dude, I don’t even really feel like being here anymore but whatever, I’m just going to ride it out.” Now, quitting was never an option. I was just going to be like, “All right, let’s get this thing off, and you know what, it is what it is, if I get cut then that’s the way life works out.” Whereas obviously Bentley was kind of like “You know what, I think I’m gonna leave.” I’m like “What? What do you mean? I don’t even know if you can leave.” He’s like “I’m going to go back to my daughter” and all this. There is no doubt in my mind that he missed his daughter. But I think it sounds cool or something to maybe say the “I’m using my daughter” thing, but it’s really not the case. If you try and add everything up that he said, I’ve had friends say, it’s like everything he said is very contradicting and it doesn’t all add up and maybe that’s what he was trying to do. I don’t know. … Did it offend me? No, I could give a sh*t. You know what I mean, you move into this house. A lot of people are there not to make friends, you stay in touch with some people. I have a feeling I’ll be in touch with Bentley. Bentley and I talked a lot about business and we’re both entrepreneur-type guys. I’m not saying like I trust him totally, but I don’t really trust anyone in there ‘cause I don’t really know those people. I think everybody’s got a motive to be there and I think genuinely there are people that get maybe lucky and fall in love and whatnot. That’s initially why I went but then it kind of turns into, you are there to kind of maybe promote your career so to speak, as well.

How upset were you at being let go before a one-on-one date?
To be honest with you, I thought that having the balls to walk into that house with a mask on, I would’ve thought that I was potentially going to get maybe a one-on-one date with her sooner than later. I don’t know, it just kind of kept getting dragged out a little bit. I guess I was a little surprised by it, but it wasn’t straining on me or anything. I hate to say this, but — well, I don’t hate to say it, but — I’m just a very laid-back person. The way I live life is, the things that unfold in front of us and whatnot, that’s the way it’s supposed to happen. So if I was, you know, booted out of there on the third episode, that’s the way it was supposed to be, I guess. Maybe I would’ve lasted to the fifth or sixth episode if I wasn’t wearing a mask or something like that. The way I look at it is, 10 years from now there’s going to be people that remember that girl that wore the fangs or had fangs [Madison Garton on The Bachelor Season 15]. That stands out, you know, and so does a mask. So, if I go in for three episodes and I’m out, I’m sure that 10 years from now we’ll remember some idiot wore a mask.

You mentioned that you really only talked to Ashley three times, but in those three times did you feel any sort of connection and did you feel like maybe she could possibly be the one for you?
No, I didn’t really feel a connection at all. Again, I think the mask [was distracting] and the conversations, you’ve got cameras around and whatnot. You’re trying to spill out a bunch of stuff about you like right away and it’s just — I don’t know. It was never real lounging. It was never like “Hey let’s just go sit on the couch and just hang out” like you do at your house and just chill and talk and get to know somebody. So, no, to answer your question. I mean, she’s typically not [my type]. .She seems like she’s got a hilarious sense of humor and I bet you that if we were hanging out one-on-one regular without a freakin’ mask on — going to a movie and grabbing dinner or something — our conversations would be probably very normal, just like they were the night that I had it off when we were at the comedy club and we were just talking and laughing and stuff like that. She was surprised about what I do for work and who I hang out with and whatnot.

Did you really wear the mask all day every day?
No, I did not.

If you could give any message to everybody out there about your time on the show or about you, what would it be?
My message, the real message was, we do live in a society where everybody is just judged based on looks and materialistic things. Money does not matter. Everybody in there is a decent-looking guy. I’ve got a three-legged dog, you know. I do things a lot different than a lot of people. I don’t know. It amazes me how people at home watch the show and I’ve seen online — you either get it or you don’t. For me, the way I think, it’s like, a dude steps out of the limo with a mask on. It either clicks in your head relatively soon or it just flies over everyone else’s head, which I think it did a lot. The message is, you know, hey, let’s just hang out and get to know each other. ‘Cause at the end of the day, whether you’re married, engaged, you’ve got a boyfriend, girlfriend, whatever, you’ve got to get used to just sitting around the house and being bored with that person and just literally not doing all that much. ‘Cause that’s what the rest of life is, is just kind of hanging out, getting to know each other.

Credit: Rick Rowell/ABC Television Group ©2011 Disney Photo: Ashley Meets Jeff in the Bachelorette Season 7 Premiere

You seemed to spend a lot of time with Bentley. What did you think of him while you were taping and what do you think of him now that you’ve seen the show?
Jeff: Well, Bentley was my roommate. I hung out with him a lot. I just think that, 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’ve got a pretty good judge of character and can read people very well. 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 who did not immediately shun me so to speak. And Bentley was one of them. I immediately was talking to Bentley and Ames. Those two guys right off the bat were really cool. I knew what I was doing from the get-go. But I don’t know. Hard to read now that I’m seeing 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’m a pretty laid-back person, I know Bentley is. He seemed very just like disinterested and whatnot. Well he was, I guess.

At what point after being cast on the show did you decide you were going to wear mask — and why?
Good question. People that know me, my friends and family, [know] I’ve got an extremely dry sense of humor and I love comedy. The way I view things was, just in general, ‘cause I am a businessman, I own a little wine called Freaky Muscato … I just knew I wanted to walk into that house — ‘cause there’s 600 plus people that have done this show before, and I was like “Why the hell would I walk in as just regular old Jeff?” I mean, that’s easy. So I was thinking about doing a big fake mustache, you know, like Tom Selleck or something. Maybe I was going to get out of the limo eating a doughnut or something. I thought about being a fake limo driver, you know, 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 in disguise. I also had the mask idea and after talking to the producers of course they were like “I think it’s genius” and “Let’s roll with it.” I mean the whole idea behind it, as much was 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 in to this freakin’ mansion with a mask on? I mean, who in the hell would do something like that? But, you know, for me, I had a brain hemorrhage at 29-years-old, you only live once and I pretty much said that’s it, I’m just going to do it, why not, and that’s why I did it.

Were you actually there to try and find love and have a relationship, or just to make a point?
I could tell you that if you talked 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. What’s hilarious about this whole thing is that I’m a very normal, regular person and, yes, to answer your questions I do and I went there and, like I said, I can tell you that the casting directors would tell you that Jeff is just a nice, nice guy and that I do treat people with respect. But you don’t go there knowing exactly who [the Bachelorette is] going to be. If you get lucky, you walk in and there’s chemistry or something and 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 in the whole time that I was there. I just went in with a different angle.

If you could have a do-over, after watching how it went down — how Ashley said you were older than she thought and that you told her about your illness — do you think you would do it differently this time?
No, actually I don’t. Because, I mean, I think the three oldest guys were myself, 35, the Tim guy on the first night — he’s 35 — and I know JP is like 34. What’s funny is I get people that tell me every day that I look really young for my age. I run six miles every day, I don’t know. I guess I don’t think I look old for my age or anything like that. To answer your question, no I don’t think I would do it differently. It was just one of those things where I was like, I knew that no matter how I was shown on the show or what the perception of me was, whether it’s weird, strange, odd, yeah. I’ve got a company called Freaky and I sell wine that’s called Freaky. There’s so much meaning behind it and that’s why I probably wouldn’t change it now.

Was there anyone in the house who as particularly nice or not so nice? What was your reaction from the guys?
When I walked in there, in the foyer of the house, you’re supposed to walk over to the right; I kind of stepped over to the left and I was like, I kind of closed my eyes and I was like, you know what — pardon my French here, everybody — but I was like “You know what? F**k it.” Seriously. I was like “I’m just going to go in there and just roll.” The second, I mean literally the second, I walked in, people started to make fun of me. And I knew that was going to happen. I am a very confident man. I knew what I was doing. Ames, Ames never — he was just a nice guy. Ames and I are very similar. Ames is obviously an educated guy. I’ve got my MBA. Bentley’s an educated guy. Bentley apparently has an MBA. Those two guys were the guys I pretty much spoke to the whole night. 

Credit: Wetpaint Photo: Masked Man Jeff From Season 7 Bachelorette

We got off easy. Jeff Medolla considered wearing a huge fake Tom Selleck mustache on The Bachelorette premiere. We could’ve been stuck staring at that for three episodes.

Jeff knew he wanted to go into the show using a disguise and “flip the script” in some way. He settled on a mask, becoming Masked Jeff in his grand “social experiment” that was less about an earnest statement about appearances than a way to show off his dry sense of humor and love of comedy. He calls it “a joke with an awesome message.” He’s a big prankster and apparently all his friends are laughing their asses off about it.

The producers, of course, thought his mask idea was “genius,” Jeff told reporters on Thursday’s media conference call. “I mean, who in the hell would do something like that?” This guy!

Jeff Medolla, 35, an entrepreneur from St. Louis, Missouri, has no regrets about his mask stunt and wouldn’t do things differently if he could go back and do it all over again. (But please, God, don’t let him.)

Despite his gimmick, Jeff calls himself a nice, genuine guy. He’s also pretty interesting — he’s in the wine business, his friends are rappers, he adopted a three-legged dog, he plays hockey, etc. It’s too bad he didn’t just go with that instead of his mask trick, but he wanted to be memorable.

Not that it matters, since most of the questions on the conference call were about his roommate in the house, Bad News Bentley Williams. They are both laid-back guys who don’t drink and have several things in common, Jeff said. (Like not really giving a crap about being there.)

Jeff said Bentley and Ames Brown were both “really cool” to him and the only people in the house who didn’t “shun” him. Jeff also thinks Bentley will have no problem with women after the show, since a lot of women like a**holes. (Ugh. Sad, but true.)

He wasn’t offended by Bentley’s comments about the guys as “tools” and “idiots” for believing him. He also plans to keep in touch with Bentley. However, he “didn’t really feel a connection at all” to Ashley, since he only talked to her three times. He thinks only three or four guys really felt a connection with Ashley since nobody is told who will hand out roses ahead of time.

Still, Jeff said one of the bachelors who seemed genuinely into Ashley was our beloved “Cupcake” JP Rosenbaum — which is a relief since we were starting to wonder if any of the guys on this show even noticed Ashley was there, amid their own self-promotion.

Read on for more highlights from Jeff’s extremely long interview:

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Credit: ABC Photo: Bachelorette Sneak Peek! Jeff Takes off His Mask for Ashley in Season 7, Episode 3