Jeff Medolla on Bentley Williams: Seems lots of girls like asshole guys

Jeff Medolla thought he had struck upon a great idea when he decided to wear a mask during his initial time on Ashley Hebert's edition of The Bachelorette.


But while the mystery of Jeff's appearance and the mask's suggestion that Jeff wanted to be evaluated on his personality got him through The Bachelorette's first two Rose Ceremonies, he didn't fare so well after he finally decided to take his mask off. After spending some additional time with the now maskless man during a group date, Ashley opted not to give Jeff a rose at the season's third Rose Ceremony, resulting in his elimination.

During a conference call with reporters on Thursday, Jeff discussed his The Bachelorette experience and what his real impressions of fellow bachelor Bentley Williams were while on the show and how they've changed while watching the season unfold alongside viewers.

During the interview, Jeff told Reality TV World why he really wore the mask, whether he really had planned to take it off sooner, why Bentley's decision to quit the show wasn't a surprise to him, and how Bentley allegedly was far from the only bachelor who just wasn't that into Ashley.

Click here to read the first part of Jeff's lengthy conference call -- which also included when he decided a mask was the best approach to his The Bachelorette appearance, what his impressions of Bentley were during the show, whether he feels Bentley's "dot-dot-dot" exit was legitimate, and what he thinks Bentley's The Bachelorette intentions were.


Below are additional highlights from the reminder of Jeff's call with the press -- in which he explained who befriended him in the mansion when the other men "slayed" him, whether he was blindsided by Bentley's privately expressed condescending comments about all the bachelors, which man he believed would be a great match for Ashley, whether he felt the mask put an unbreakable barrier between him and Ashley, why he claimed he didn't feel a connection with The Bachelorette star at all, and what made him think Bentley will have no problem "getting girls" in the future.

Were you hurt at all by anything Bentley said or did, especially since he talked a lot of crap about Ashley and the guys in the house and you were apparently friends with him?

Jeff Medolla: I think unfortunately, we live in a country where scandalous-type sh-t sells and nice guys are kind of like "eh." All of a sudden, you've got this asshole dude and all of a sudden, that's like what totally sells.

I don't think Bentley's going to have any problem getting any girls to be honest with you, because it seems like a lot of girls like asshole guys.

I don't think Bentley is a total asshole. I don't think he's a total asshole, I just think he liked the camera and was 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 admit that I didn't totally -- my whole situation was very unique too.


With the mask, I was kind of getting to the point where I was 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, "Alright, let's get this thing off and you know what? It is what it is. If I get cut, then that's the way that life works out."

Whereas Bentley, he was just kind of like, "Hey, you know what? I think I'm going to leave." And I'm like, "What?! What do you mean?" I'm like, "I don't even know if you can leave." He was like, "Oh, I'm going to go back to my daughter," and all this. There's no doubt in my mind that he missed his daughter, but I think it sounds cool or something to maybe say, "Yeah, I'm using my daughter thing, but it's really not the case."

I don't know. You try to add everything up that he said. I've had friends say, "Everything he said is just very contradicting and it doesn't all add up. Maybe that's what he was just trying to do." I have no idea, but did it offend me? No, I could give a sh-t less. 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 that I'll be in touch with Bentley. Bentley and I talked a lot about business and we're both entrepreneur-type guys, and I don't know. So, again, I'm not saying I trust him totally, but I don't really trust anyone on there because I don't completely know those people.

I think everybody's got a motive to be there, and I think genuinely, there are people there that maybe get lucky and fall in love and what not. 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. I don't know.


When you mentioned that the guys in the house "slayed you," was there anyone in particular that was nice to you or did anyone surprise you by standing out for being too nice or mean?

Jeff Medolla: Okay, so when I walked in there and I was in the foyer of the house, you're supposed to walk over to the right and I kind of stepped over to the left. I was like, "Okay." I kind of closed my eyes and I was like, "You know what?" Pardon my French here everybody, but "F**k it."

I mean seriously, I was like, "I'm just going to go in there and just roll." The second -- literally the second -- that I walked in, people were starting to make fun of me, and I knew that was going to happen. I am a very confident man and I knew what I was doing, and I don't know.

[Ames Brown], Ames never -- like Ames was just a nice guy. Ames and I, I think, 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 are the guys I pretty much spoke to the whole night. I didn't have many people to talk to.

I would kind of slip away and go take some time off in terms of chilling out in another room where there wasn't people and what not just because it was one of those things where it was like -- it was very seventh grade-ish. It is what it is, you know?


Was there anything that surprised you about any of the bachelors or did you learn any secrets?

Jeff Medolla: No, not really. I guess, I mean, I think a lot of people are always fairly surprised at some of the things that Bentley was doing in the one-on-ones and stuff like that, so. My thing is, is I'm a former hockey player, okay? Talking sh-t is part of the game. So what good does it do to talk sh-t when you go back to the locker room?

So me, if I'm going to talk sh-t when I used to play hockey, I'm going to talk sh-t to somebody's face. So that whole thing, you know, certain people play the game and what not, but you've seen old contestants who have been on the show who are outspoken and what not. But you give credit to those people, because they'll just straight talk sh-t to your face and be like, "What?"

But then, I don't know. I think it's easy to go talk sh-t in front of a camera behind everyone's back and stuff like that. So, I didn't talk sh-t about anybody when I was there. I was just like, "You know what? It is what it is and they don't have any footage of me ever saying anything negative about anybody."

What did you end up doing with the mask?


Jeff Medolla: A lot of people have asked that question, and I've seen online a lot of people saying [I shouldn't have burned it when I left], "Holy crap. That guy could have sold that thing for a ton of money." I had two of them, so one was for that and I have one more, so I don't know what I'm going to do with it.

For me, again, it was just -- I don't know. That's a good question though because I've had hundreds of people say, "Are you going to sell that mask?" (Laughs) And I'm like, "Well, I don't know. Maybe I will."

You said Bentley was a "tough read," so would you say you were blindsided by the stuff he had said to the camera, especially when he called you guys idiots and bragged about how he had fooled you all?

Jeff Medolla: I think I personally, I think I kind of had -- I think he's 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 of my health and I run a lot. Don't get me wrong. Occasionally, I'll have a glass of wine and I sell wine. I have a winery and what not, but I'm just not that big into drinking. So, him and I -- it seemed like we had a lot of things in common.

I don't know. I think it might just be like some of the things he got a little loose with in those one-on-ones. For me, I think it would have been easy just for me to -- I had a frickin mask on for Christ sake. I could have easily gone in there and been like, "Screw all these fools. I don't need this bullsh-t."


I could have sat there and been like, "I'll whip all these dudes' asses," or something, but I didn't do that because it's pointless. It's easy to go do that. That's the easy thing. So, I don't know. I think I'm confused a little bit on it, but yet again, it's like ratings and TV and I don't know. (Laughs) I don't know.

Of everyone who is left on The Bachelorette, who do you think the right guy is for Ashley and do you think she'll end up engaged?

Jeff Medolla: Okay, so I think maybe she'll end up engaged. It's hard to say. I think I could tell that there were a few guys that were really -- seemed like they were sincerely into her. One of course, everyone's kind of talked about [J.P. Rosenbaum]. J.P. seemed like a nice guy. I did talk to him once, but again, the reception of me was never real warm.

It wasn't like a bunch of dudes over there talking, I'd come over, I have to really engage in the conversation and try really hard. I've never had to do that. Some of my best friends are African-American and I get along with everyone. So, to answer your initial question, I like J.P. -- J.P. seemed like he was actually really genuinely into her. So, yeah, I'd go with him.

Do you think wearing the mask hindered your opportunity to really get to know Ashley? Do you think that put any type of barrier between you two in that the focus became not on who you were on the inside like you had hoped, but that you were labeled the guy in the mask?

Jeff Medolla: Yeah, well her and I again, I spoke to her three times. That was it. You only get a handful of minutes with her, and it was a barrier of course, but it was also a joke. It was also a joke with an awesome message. I'm a big prankster and I had absolutely [no idea of] -- of course I've never been in that situation -- how much time you'd get with her.


I didn't know if she'd be over there every single day talking to us or hanging out or whatever, you know what I mean? My first initial thought was, "How frickin hilarious would it be to show up to a big old party where everybody's nice looking and everybody's relatively successful and just not show your face?" That's just kind of what I did.

After that night though, it was kind of like I didn't realize how a long time would go in between the next time I even saw her again. I didn't know if she was going to show up the next day or whatever and then I'd be like, "Hey, what's up? Alright, I'm taking it off," or something like that. But no, I have no regrets about what I did because there was a lot of me behind it.

Did you ever worry that Ashley let you go because she couldn't get over the joke, the fact that you wore a mask?

Jeff Medolla: You know, the day that I took it off -- that night we went to the comedy club -- I did get about five minutes or so to talk to her, and we were talking and of course that was that night she had a tough time with the comedy stuff and whatever. She was absolutely surprised when she found out a little bit about me.

Again, I'm in the wine industry. I work -- some of my best friends are rappers who are in on the wine with me. I was telling her a little bit about me like, "Oh, I played hockey in college and I got a three-legged dog that I adopted," and she was telling me about how she just adopted a shelter dog as well. I thought it was good conversation, but yeah.

Had that been the first night, like the way that everyone else does it? I think it maybe could have been slightly different. But at the end of the day, she's 27. I'm 35. Maybe I was a little bit too old for her. I have no idea, you know?... That [fifteenth-season The Bachelor] Brad Womack guy -- that dude is 38-years-old, okay? So the whole, "He's 35," I was like, "What?! Okay, whatever." 


You said you only talked to Ashley three times, but in those short moments, did you feel any type of connection with Ashley? Did you ever think she could have been the one for you?

Jeff Medolla: 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 what not -- and you're trying to spill out a bunch of stuff about you like right away. I don't know. It was never really lounging.

It was never like, "Hey, let's just go sit on a couch and just hang out like you'd do at your house to just chill, and talk and get to know somebody." No, she's specifically not -- I date -- I don't know. I usually date girls with darker hair and whatever.

I'm sure she's got a hilarious sense of humor and I bet if we were hanging out one-on-one on the regular without me having a frickin mask on and we'd go to a movie or dinner or something, that our conversations would be probably pretty normal just like they were the night 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 what not.

What do you wish viewers had gotten to know about you besides just that you wore a mask?


Jeff Medolla: Well, you know, I guess the disappointing part of that is that my one-on-one interviews were kind of just me talking about who I am as a person. Again, I'm a smart businessman and I knew what I was doing. I knew as much as the mask would draw attention to me -- I put an "X" on my face, so to speak -- I also can relate it back to my business.

You want to think I'm a freak? Go ahead, think I'm the biggest freak in this country, and oh by the way, let's go sell some Freaky Muscato wine or Freaky vodka. Those are the things -- that's me. I knew that as funny as it would be, think about that. Who in the hell would be in a pool swimming with a mask on? All the funny things I did -- all I did was funny things with the mask.

That's all I did, but my character on the show was "Mr. Serious Guy," you know? You never see me smiling or laughing, and I guess that's kind of what's disappointing, because to me, I don't care what people think about me. I don't care what millions and millions of people think, that I'm odd or strange, that was the point too. I can relay it back to my line of work.

I want you to think I'm weird. I want you to think I'm strange. Go ahead. But I'm not, and that's what's awesome, because all my friends just laughed their asses off when they're watching it. When I'm reading the newspaper on the toilet, making stuff up as if I'm going to buy a boat with no motor and Bentley's fixing his hair, we were just having a good time, you know?

Did you really wear the mask all day everyday?

Jeff Medolla: No, I did not... There's people that were like, "Oh my God it looks like his face was smashed down."


Did you learn anything new about yourself while you were on The Bachelorette from the experience?

Jeff Medolla: Well, it didn't change me as a person. I really, I don't take myself real serious at all. I make it a point everyday to laugh and smile and try to put smiles on people's faces, and that's the way I am. I think that if there's something a little bit that I learned, just a little, is that I even had more -- pardon my French again -- but more balls to do that.

I've had so many people reach out to me. They're like, "Dude, I could never do that." I was just like, "You know what? I could have bailed. I could have not done it and whatever," but I just stuck to it and now I don't regret it at all. I think it's hilarious.

What hockey experience do you have?

Jeff Medolla: I played juniors and then I moved away in high school to go play up in Michigan. I'm an extremely competitive person, and don't get me wrong, when I'm sitting there with a mask on and there's people talking sh-t, I've obviously fought many times in hockey before. It was very tempting to take the thing off and knock a few people out. (Laughs)

I'm pretty chill now, you know? At 29, I had that brain hemorrhage and I don't live like that anymore. I still play hockey twice a week, but that's just what's been so funny about the whole thing. People took it so frickin serious, and really? The guy's got a mask on in the pool swimming laps? Really? That's what's so hilarious about it though. (Laughs)


If you could give any message to everybody out there about your time on the show or about you, what would it be?

Jeff Medolla: My message, the real message, was we live in a society where everybody is just judged based on looks and materialistic things. I could be sitting here with -- money doesn't matter.

Everybody in there was a decent looking guy, and I just, I don't know. I've got a three-legged dog, you know? I do things a lot different than a lot of people, and I don't know. I guess it amazes me how people at home will watch the show and I've seen online, you either get it or you don't.

For me, the way I think, is that a dude stepped out of the limo with a mask on. Either it clicks in your head relatively soon or it just goes -- it flies over everyone else's head, which I think it did a lot. It's like -- what I mean by either you get it or you don't -- everyone else is showing their face, so I did the complete ass opposite of it.

That's just how I operate and that's the truth. "Hey let's just go out and get to know each other." Because at the end of the day, whether you're married, engaged, you got a boyfriend, girlfriend, whatever, you gotta just get used of sitting around the house and being bored with that person -- literally just not doing all that much.

That's what the rest of life is. It's just kind of hanging out, getting to know each other.






About The Author: Elizabeth Kwiatkowski