Rollo, 45

What do you do for a living?
I work at City College of San Francisco as a campus security aide. Like a glorified security guard, but I have police training.

Does that get you any dates?
No, I'm one of the few people who get introduced by their profession. You know when you walk into a party and you don't know anybody? I'm always introduced as "the police officer... what's your name again?" It's like that.

How have you secured dates in the past then?
For pickup artists, the philosophy is "If you ask out a hundred women, one's bound to say yes." When I want to go out with someone, I just walk up to them and say, "Hi, my name is Rolando," and I try to make them laugh.

What are you attracted to?
Well, when I was a Spanish kid in my punk-rock phase, my girlfriend had a purple mohawk with a tattoo of a rat on both sides of her head. But now I'm basically attracted to women who are unique individuals. When you went to the prom, there were fifty girls wearing different versions of the same dress. I went for the girl who decided to wear something totally different. I like outspoken people with their own opinions. Have you traveled? Is your family as dynamic and crazy as mine? And I like women who have intense eyes like you do — don't be surprised if I ask you out before this is over.

Thanks for the heads up! Okay, guessing from your dating philosophy, I'm assuming you've been on a lot of dates. Have you ever been married?
Yes, twice. When I met my first wife, Steffi, I had just gotten out of a bad relationship. My ex-girlfriend had been abusive. Looking at me, you wouldn't think a woman of your size could beat the crap out of me on a daily basis, but it happened. When I broke up with her, I was in that stage where you're just unsure of yourself and don't know how it all happened. I saw Steffi on the street talking on a payphone in German. I know a little bit of German, so I approached her and asked her out. I took her to dinner in Chinatown. We went dancing. I took her to the Sky Lounge at the Marriott. Everything was going good. She spent the night, but nothing happened. I was a gentleman. And the next morning, we went to City Hall and got married.

The next morning?
Yeah. She wasn't a citizen and was going to go back to Europe. On our date, I told her I didn't want our night to end and that I wished she could stay. She also wanted to stay but there wasn't a way for her to do that. I offered to marry her and she didn't believe me. A lot of, "No, you won't," "Yes, I will." It was like a gun-fighter scene — who's going to blink first? I guess neither of us blinked, and we got married.

And afterwards?
Afterwards we went home and consummated the marriage. Twice. And even after that, I was faithful to her as a husband, but it only took her two months to turn around and stab me in the back. We were together off and on for ten years.

You seem to be quite the romantic.
I am. I like candlelit dinners. I like surprising women with the little things that make a relationship special. Imagine we're in a perfect world and we're dating. I take you to the Ritz Carlton Hotel. But before we get there, we stop by Jessica McClintock to pick you up a dress because we're going to do something nice. I arrange for the hotel to get a limo. While we're away, I arrange for the bath to be prepped with jasmine flowers, rose petals, candles, everything. Although we've had a substantial meal, there's always room for a little imported Belgian chocolate. And when we get back to the room, the soft music's playing and we dance.

I don't know. I've never been that kind of girl.
Well, you know, I bet for five minutes — maybe an hour — you probably could be.

Didn't you say you liked girls who departed from the norm, though? Those moves seem to be cut out for a pretty standard girl.
Yeah, but every person has their own version of romance, and I'm a classical romantic. What can I say? I read way too many books. Damn Jane Austen. I'm serious! My father, may he rest his soul, always said, "You treat a woman like a princess and a princess like a queen."

What about your second marriage?
My abusive ex-girlfriend had a friend named Jennifer who I reconnected with fourteen years after I first met her. I was visiting New York, where she was living at the time, and we started dating. And after she moved back to the Bay Area, we got married.

Was it as tumultuous as your first marriage?
In the beginning, my second marriage was good. I think I'm at fault for putting too much stress on the relationship. We moved to the East Bay after a while and people, you're not going to believe this, she came out of the closet. I was being treated really bad. I couldn't even get my wife to go out on date with me on a Friday. So it was like, eight or nine Fridays in a row and I blew up at her and she told me. It lasted four years and now we're in the process of getting a divorce.

Was it a shock?
I didn't notice it, because I was trying to give her a chance to be independent and do the things she wanted to do. I should've noticed something when she joined roller derby. I should've noticed that when she wanted to come home early from events for roller derby practice. We were getting to the point where she wouldn't want to spend her birthday with me because she wanted to be at roller derby. I should've taken it as a sign, but I thought it was because she was a type-A personality who wanted to absorb everything and move forward with it.

Had she ever been a relationship with a woman?
I heard rumors afterwards, but nothing that I know for sure.

So is she a lesbian or bisexual?
I think she's bisexual. I'm not going to fault her for being either — I just wish she had told me sooner.

Do you think she knew and got married to you anyway, or that she discovered her sexuality while she happened to be with you?
I think she knew and didn't tell me and was trying to scare herself straight and it didn't work.

You said you're a classic romantic. After all this, do you still believe in marriage?
I don't think I'll marry again. You can still have romance in your life. You can still be with someone and not marry them. You can still live with someone and treat them as your equal. This all sounds so Edwardian.

Well, the way you put it, you're not at fault for the failure of your marriages. So why would you stop here?
Because you can tell people it's not your fault, but people will still look at you as "twice divorced." When your first wife tells you over the phone that she's cheated on you twice, when your second wife comes out of the closet. These things weren't my fault. But I think I'm just jaded right now. Maybe I'll change my mind later, but I don't know if I will. I can still be romantic. I can still take you ballroom dancing, to a jazz bar.

How do you bring romance into such a cynical dating climate?
Be the little engine that could. If you try and it drops, try and try again.

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