Millionaire bar owner takes failed search for love to Bravo

On any given night, Jimmy D'Ambrosio says his three Chicago bars are filled with any number of women who would gladly go out with him.

But the 31-year-old is looking for love. Or at least he was when he tried to find it on Bravo's "Millionaire Matchmaker."

The results were a far cry from successful, but he claims it made for great television. Fans of the show that airs locally at 9 p.m. today will be able to judge for themselves. D'Ambrosio is even hosting a viewing party at his Citizen Bar at 364 W. Erie St. in Chicago and is prepared for what he calls a "bad edit."

On the show, matchmaker Patti Stanger sets up well-off men on dates with eligible women. A typical episode goes something like this: Stanger meets the client, tells him how to fix himself up, interviews the single women, yells at the client for ignoring her advice, introduces the client to a bevy of women, and then the client goes on a date that is either preposterously romantic or epically disastrous.

The Naperville-raised D'Ambrosio knew what to expect from reality television because his sister, Nicole, made it through several rounds of Donald Trump's NBC show "The Apprentice" in 2007. But the entrepreneur and professional poker player admitted he ignored his sister's advice and let it all hang out for the show.

D'Ambrosio talked about his search for love, his roots in Naperville and why he wouldn't change himself for the show.

Q. Why can't you get a date?

A. I have many dates. But the issue is wanting a highly intelligent and highly attractive girl with a big heart, and those aren't growing on trees.

Q. You're pretty young compared to some of the other guys featured on this show. Why are you looking to settle down now?

A. At the time I filmed the show I was looking to settle down. After that experiment it reminded me how happy I am to be single and free and doing my own thing.

Q. So I take it the girl you dated on the show is not going to be at your viewing party?

A. The girl I dated seemed very sweet and smiley at first. And then upon getting to know her better and the champagne kicking in, I realized she didn't carry much depth and weight to her personality. With me being somewhat forward to a fault, that led to the fireworks you'll see on the show.

Q. How did Patti take that?

A. In the editing of the show it's making it out to look like Patti hated me, but she never showed that to me directly. When she was around me she was like, "Can we put the Jimmy D charm in a bottle and distribute it to all the guys out here?"

Q. Was Patti as mean as she comes across as on the show?

A. Not to me, but I would not want to be one of the poor guys on the production team because she did not treat them very kindly.

Q. What advice of Patti's did you follow, and what advice did you ignore?

A. The advice I followed was be sure to pay more attention to the girl and I thought I followed it until I lost interest in the girl. The advice I didn't follow: She had me speak to a speech therapist because she wanted me to lose my Brooklyn accent. I made it very clear I've never been to Brooklyn. And the guy goes on and on about how girls don't like that, but all the girls were telling me they liked the way I talked.

Q. Most of the guys on this show come off a little creepy. Aren't you afraid you're going to be edited that way, too?

A. I wasn't worried about how I was going to come off. In my preproduction interview I told them I'm not some dot-com dork. I was in a boys home at 17 and worked my way from the ground up and had street smarts before business smarts. The problem with most of the guys on this show is they are uncomfortable around women.

Q. You were in a boys home? I thought you grew up in Naperville?

A. My father was a less-than-admirable role model. The long story short is that there were a lot of issues with that and I ended up in a boys home in Naperville. But I figured I could feel sorry for myself or I could use that to make myself a better person.

I graduated from Naperville Central in 1995 and I started a painting business painting houses all over Naperville when I was still in college at Northern Illinois. I met a lot of good people and I had an absolute blast doing that and I miss it. I think I painted almost all the houses in Ashbury. I miss being out painting and getting a tan, listening to great tunes with my buddies and seeing the results of my work.

Q. Why are you screening this at your bar without knowing how it will be edited?

A. I have no fear. I know who I am. I've been given heads-up enough to know I'm going to get what they call a "bad edit." I did not get where I got worrying about what everyone thinks about me. Some people are going to like me and some people aren't.

Q. Your sister warned you about what to expect though, right?

A. She gave me advice to be aware that everything I said would be edited, so she said to be careful. I did not heed that advice at all.

Q. How will you know you've got the right girl?

A. If she beats me at poker I would find that an attractive quality. Then we have to run to the altar.

Q. What's been your problem with finding love?

A. Most of the time I think it's been I'm not ready. I've been a lifetime bachelor. I was once engaged but broke it off when I realized I was not ready. The show did reaffirm that when I do settle down it will have to be a girl with Midwestern values, not a Hollywood girl who has too shallow of a personality.