Before the June 20 event, O'Hara spoke with Windy City Times about the contest.

Windy City Times: How did you find out about this contest?

Brendan O'Hara: On Facebook. You know how they have those ads on the right-hand side of the screen? There was one that read, "Are you gay and are you single? Then you could be America's next gay bachelor." I clicked on it, out of curiosity, and it looked like a [ legit ] contest, so I said, "What the heck? I'm gay and single. I'll float a few pictures and answer a couple of questions." I didn't think anything of it, and on May 1 they sent me an e-mail, saying they chose me to represent Massachusetts in this contest. [ Laughs ] It was a total surprise.

WCT: So do you have any idea how you were selected as one of the top five finalists?

BOH: There were different levels. The first level was state [ rep ] —the panel of judges at MyPartner.com chose one person from each state. Between May 1 and 31, the top five [ vote-getters ] got to go to San Diego.

WCT: Once you get there, it'll be a pageant-like atmosphere.

BOH: Right.

WCT: And what will the categories be?

BOH: They just sent me a six-page PDF about it, and it seems pretty intense. They're going to ask us a few questions, do a runway show modeling Rufskin denim.

WCT: And what does the winner get?

BOH: The title, a getaway for two valued at $2,000—they call it a matchmaking package courtesy of MyPartner.com. I asked them about it, and apparently it's a concierge service, if you will, to help you find a partner.

WCT: What types of questions are you expecting? Keeping in mind Carrie Prejean, what would you answer if they ask you about same-sex marriage?

BOH: Well, I'm definitely for it; I hope to be married myself one day. I live in Massachusetts, so a bunch of my friends are married—some with adopted children and some with children from past [ relationships ] . Obviously, I'm living in the right state, but I'd love to see the federal government pass a law allowing same-sex marriage.

WCT: Concerning June 20, are you nervous? Excited?

BOH: I'm definitely nervous. [ Laughs ] I've never done anything like this. I'm a musician, and play music on the streets of Provincetown in the summer; it's my second source of income. But I've never done runway. It'll be anxiety-provoking, but it'll be a lot of fun.

WCT: So you've been practicing that walk and watching America's Next Top Model?

BOH: [ Laughs ] No. I figured that being myself has gotten me this far, so why would I change anything now?

WCT: That's a great way to look at it. What can a guy do to get your attention?

BOH: One of the first things I notice is the face—eyes and a smile catch my eye. Eyes are a pretty subjective thing. Someone who has a nice smile and likes to smile catches my eye, too. I also like somebody who dresses well—not like Gucci and Prada; I just like when a guy cares about his appearance. I also find business attire very attractive.

Note: After the contest, O'Hara e-mailed, "Everyone was so much fun, we were treated very well, the entire weekend was very professional, and [ it was ] all for a good cause: Much of the proceeds go to benefit Marriage Equality and, I believe, the 'NOH8 ( No Hate ) ' campaign in [ California ] ."