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 with Reality TV World -- including why he really wore the mask, whether he really had planned to take it off sooner, why Bentley Williams'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.
Also check back with Reality TV World on Friday for more from Bentley's extensive media conference call.
Reality TV World: How upset were you that Ashley eliminated you before you even got a one-on-one date with her? What do you think led to her decision of letting you go so early in the competition?
Jeff Medolla: To be honest with you, I thought that having the balls to walk into that house with a mask on, I would have thought that I was potentially going to get maybe a one-on-one date with her sooner than later, you know? I don't know. It just kind of kept getting dragged out a little bit, and I don't know.
I just, I don't know. I guess I was a little surprised by it, but it wasn't straining on me or anything like that. I hate to say this but I mean -- well I don't hate to say it, but -- I'm just a very laid back person.
I was just -- the way I live life is the things that unfold in front of us and what not, that's the way it's supposed to happen. So, if I got booted during the third episode, that's essentially the way it was supposed to be, I guess.
Maybe I would have lasted to the fifth or sixth episode if I wasn't wearing a mask or something like that, but the way I look at it is 10 years from now, there's going to be people that will remember that girl [fifteenth-season The Bachelor bachelorette Madison Garton] that wore the fangs or had fangs because that stands out and so did the mask.
So, if I go in for three episodes and I'm out, you know, I'm sure that 10 years from now, people will remember some idiot that wore a mask.
Reality TV World: You said you had no regrets, but you were planning on taking the mask off sooner, so had you really planned on taking it off during the second episode had you not been interrupted? Do you wish you could have followed through with that or do you think it wouldn't have made any difference?
Jeff Medolla: Yeah, I was planning on taking it off that night and then obviously got interrupted, and it was a little awkward because we're in a stairwell thing or something and I was just like, "Oh, well, how hilarious is this going to be to just be standing up at the second Rose Ceremony with a mask on?" But you know what, that's the way it was.
Essentially, I knew that I pretty much made it very clear that the thing is coming off real fast, and as soon as I see her again, it's done. That's kind of what happened, so.
Reality TV World: I know you already touched on this a little bit, but did you have any idea how much Bentley disliked Ashley while on the show or did he attempt to make all the bachelors in the mansion believe he was in it for love just like the rest of you? I know you also talked about how you played sports and it's common to trash-talk your opponents in sports, but Ashley wasn't your opponent, so what was your reaction to all the horrible crude things Bentley said about her during his private interviews?
Jeff Medolla: To answer the first part of your question, I don't know if he told other people this because I don't think a lot of people -- I don't think he -- he was friends with everyone in there, but he was always just really kind of disconnected with like not wanting to be there. It was really obvious. He was just kind of lounging around, just kind of, I don't know -- just disconnected, I guess.
But when I would talk to him, and we would just be hanging out in our room in our bunks and what not, I talked to him for hours and hours about how he just wasn't that into her, and he's just not sure if he wants to be there anymore, and that's when I would just kind of be like, "Hey dude, I don't know if you can just leave. I don't think you can just walk out the front door."
He's like, "Well, I'm going to go back and be with my daughter. I miss her terribly," and all this. So, I mean, I think when you're in that situation and you go in and you don't know who the girl's going to be, I think -- me personally -- in the past, people can correct me if I'm wrong, but sometimes in some seasons, people show up knowing who the girl is.
I think you can make that decision at home, "Well, I kind of liked that other girl a little bit more. Eh, I don't know, she's really just -- I'm not attracted to her. I'm not going to go do the show." I think you have a more honest group of guys showing up with 25 of them who are willing to hardcore compete than when you just go out there and you don't know who it is.
Maybe only three or four guys there were legitimately into her, because you go [into the show] blind [not knowing who is the Bachelorette] where there could have been 25 guys that would have liked [her if they'd announced who it was before filming] -- I don't know. I just don't know why they changed that or whatever.
Hopefully, that kind of answers your question, but I think everyone there liked Ashley. It's just you don't know who it's going to be when you go there, you know? So he obviously, maybe he thought it was going to be someone else or something like that. I have no idea.
Reality TV World: I also want to clarify, you seemed to suggest you believe Bentley just said he was leaving because of his daughter because it was "cooler." So can you elaborate on why you think he really left? Are you saying you now believe it was because, as the show showed, he just wasn't into her?
Jeff Medolla: I think it was two things. I think he -- I disagree that -- I know he missed his daughter, and for him to say, "Oh, I'm just using that as an excuse, it's not really about my daughter," I disagree. What guy would not miss his daughter? I mean of course you miss your daughter, but I think it's two things. I do think he missed his daughter, and I do think that he was not into Ashley.
He's just like, "I just don't want to be here anymore. I want out. I want to leave," and he's been saying that for days. I was like, "Dude, I don't know if you can go anywhere," and what not, and finally -- we were up late that night before he left. I was in the van with him and we were talking in the van for an hour.
It was him and I sitting next to each other, and we're talking and we're up until like four in the morning, and we were talking. Then sure enough, I came in the room and he was packing his stuff up and leaving. So, he just said that he just knew when he woke up that morning that he had to leave.
Reality TV World: What was your reaction when William Holman took his jokes too far at the roast? Do you think he was out of line or do you believe that Ashley was just maybe too sensitive about certain subjects and overreacted?
Jeff Medolla: No, I think Ashley's a good sport for anyone to do that. I mean, I've definitely gotten some -- I've gotten more tough skin since I've done this, because I'm an idiot and I sit there and read some of that crap online. I'm like, "Damn, those people don't even know me and they're saying all this s**t about me! Holy crap!" (Laughs)
I think William definitely did go way overboard. Most of the guys -- all the guys there had a few cracks at Ashley -- just one or two, and then they moved on and everyone ripped on all the guys. Okay? That's just the way it was, and I remember me thinking like, "I don't even know Ashley. I don't even know what I can say about her." So, I talked about all the other guys.
Then William, he didn't say anything about any of the guys, and he just ripped on her for like 20 minutes or whatever. I don't know. I know everybody was shocked, and I would never in a million years ever do anything like that. There are certain people that try to be funny, and then there's certain people that just are funny. You can put two and two together there.
Also in the call, Jeff told reporters 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.
You seemed to have spent a lot of time with Bentley. What were your impressions of him while you were taping and then how did your idea of him change, if at all, while watching the show from home?
Jeff Medolla: Well, 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 what not my whole career and I've got a pretty good judge in character and can read people very well.
My situation walking into that house was treating it like a social experiment. I knew what I was getting into. I knew I was going to walk in and get slayed immediately by pretty much everybody with the exception of a few people there that did not immediately kind of shun me, so to speak.
Bentley was one of them. I immediately started talking to Bentley and [Ames Brown]. Those two guys right off the bat were really cool. I knew what I was doing from the get-go. I don't know, yeah. He's hard to read 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.
Bentley wasn't happy to be there because of Ashley or because he didn't want to be on the show?
Jeff Medolla: I just think Bentley's demeanor is -- I mean, I'm a very laid back person. That environment for me was a lot different than for most people that have ever walked into that house.
So, it would have been easy to just walk in and be like, "Hey! What's up everybody? My name is Jeff and I'm successful too," and what not. But for me, I think because I'm a laid back person, I think Bentley is, but he seemed very disinterested. That's kind of how he was, I guess.
At what point after you were cast on the show did you decide you were going to wear the mask and why?
Jeff Medolla: Good question. People that know me -- my friends and family -- I've got an extremely dry sense of humor, and I love comedy, okay? The way I do things was just in general because I'm 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'm like, "Why the hell would I walk in as just regular old Jeff? That's easy." So, I was thinking about doing maybe a fake mustache like [actor] Tom Selleck or something, maybe I was going to get out of the limo eating a donut or something.
I thought about being a fake limo driver with a hat and gloves and really flipping the script around and really throwing everyone off. That's how I operate and I knew I wanted to go in [the mansion] 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." (Laughs) So I did. The whole idea behind it, as much as it was a joke, there was great meaning behind it.
There is a great message, which is, "Don't judge me for what I look I look like or the money that I have or materialistic things," and how hilarious would it be to walk in to this frickin mansion with a mask on?
I mean, who in the hell would do something like that? For me, hey, I had a brain hemorrhage when I was 29 years old. You'll only live once, and I pretty much said, "F it. I'm just going to do it. Why not?" That's why I did it.
Were you there to try and find love and get into a relationship or did you go on the show 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 and sincere person and I do want to find somebody that I can spend my life with. I've had great relationships with people and what's so hilarious about this whole thing is that I'm a very normal regular person, and to answer your question, I do.
I went there and like I said, the casting directors would tell you that Jeff is just a nice, nice guy, and I do. I treat people with respect, but you don't go there knowing exactly who it's going to be. So, you could 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 three times like in the whole time that I was there. I don't know. I just kind of went in with a different angle. I like to twist things and go in different.
After watching how everything went down in terms of Ashley thinking you looked older than she suspected and you talking about your past illness, do you think you would have done anything differently if you could do it over again?
Jeff Medolla: No, actually, I don't. Yeah, I think the three oldest guys were myself (35), the Tim guy [Tim McCormack] -- he's 35 -- and then I know [J.P. Rosenbaum] is like 34. What's funny is I get people that tell me everyday that I look really young for my age. I run six miles everyday, 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 anything differently. It's just one of those things where I was like no matter how I was shown on the show or what the perspective of me was, whether it's weird, strange, hot -- well, yeah.
I've got a company called Freaky. It's a wine and it's called Freaky, you know? There was just so much meaning behind it, and that's probably why I wouldn't change it, no.
The way Bentley handled things when he chose to leave the show, referencing his daughter as the main reason he had to go and telling Ashley to keep their relationship open with a "dot-dot-dot" ending despite him showing no interest in her, do you think that was legitimate? Especially in that he led her into believing they could eventually work out as a couple?
Jeff Medolla: Yeah, someone like that -- someone like my single best friend -- she's a girl and she's Mormon. They are obviously extremely strict about being with someone else that's Mormon, and I noticed there were some issues with that. Those are probably somewhat minor. I'm surprised that, again like everybody, I'm surprised that he said so many things.
I just think Bentley went way overboard. I mean, maybe Bentley literally came on the show to just say, "You know what? Screw it. I am going to throw everyone under the frickin bus, talk s**t about everyone behind their backs -- including the damn girl that's on the show -- just pull this big ass thing and then just walk away and laugh about it."
I have no idea, like again, I felt like I had a pretty decent -- I felt like I had a great read on him when I was there. We hung out a lot and what not. However, it's like when people asked me earlier like, "Am I shocked at what he was saying?" I'm not shocked at him not being interested in her because I knew that, I'm not shocked at the fact he missed his daughter because I knew that.
I knew all these things. I just can't believe some of the s**t that he said on-camera. I know there's editing or whatever, but my God, you called someone an "ugly duckling." I think that's just -- I don't know. That's just not smart. You know, I don't know. That's just me though.
I just wanted to clarify if you thought that was cool.
Jeff Medolla: Yeah, I don't think there's any guy in that house that thinks that Bentley was cool, but that's just the thing. That's his opinion. I'm sure Bentley probably thinks it was cool to do that.
That's just not my -- I would never do that. I know that probably pretty much all the other guys in the house would never do that or they would have done it or they would have done something.
I mean, heck, there's been guys on this show who have been asses before, but they're asses to people's faces. I'm not going to say any of their names, but you know how there's been guys in various seasons where they're talking s**t to the camera, and then they'll go out there and get in an argument with a guy and be like, "What dude, what? We can go right now if you want."
That's legit. To me, that's totally legit, because it's not like you're playing both sides of the fence. You're just being an ass.
So you think Bentley went into the show with the opposite purpose of you with the mask?
Jeff Medolla: Yeah, absolutely. I don't know what his intentions are, but yeah, there are people out there like that. One dude, like that [former The Hills star] Spencer Pratt guy, I guess maybe they just think it's cool to have everyone hate them or something. That's the problem. That goes back to our society and what not. That's the s**t that sells -- that and all the scandalous crap.
So, nobody cares about nice dudes -- I'm not saying that no one cares about me -- but there are nice guys on that show. There are guys that are just genuine. They're nice. Me? I've got a three-legged dog. I found him at a children's hospital, you know? I do nice things for people.
That's not really a story, but then if I'm over there talking s**t about you and I'm on a date with you and I'm all like, "Hahahaha," behind the scenes laughing about you, but then on-camera I'm kissing your neck and all this bull***t, that's just the stuff that sells. So, I don't know. Maybe that's what his plan was from the get-go.
As long as his hair looked good.
Jeff Medolla: Yeah, as long as his hair looked good, you know?
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