It seems inconceivable that starting a comedy career on a dare would produce a 20-year run that has no signs of stopping. This, however, is exactly how Suzanne Westenhoefer got her start as a comic.

She went on to be the first openly gay comic to host her own HBO comedy special in 1994 (which earned her a Cable Ace Award nomination) and appear on “The Late Show with David Letterman” in 2003.

Westenhoefer’s current U.S. tour, titled “Totally Inappropriate,” hits the Birchmere Theater in Alexandria, Va., Jan. 30. Beyond the tour, Westenhoefer has a starring role in the online web drama “We Have to Stop Now,” which is prepping for a second season as Wolfe Video is readying the first season for DVD.

DC Agenda talked to Westenhoefer this week to discuss the beginnings of her career, what it’s like to be an out comic, and her “lack of appropriate boundaries.”

DC Agenda: You began your career delivering gay-themed material to straight audiences in mainstream comedy clubs in New York City in the early 1990s. What were the initial reactions from the audience? Was it as you expected?

Westenhoefer: To be honest, I had no expectations whatsoever. I was completely surprised. I can only say I wanted to try and it went well. It went really great nearly every time, as a matter of fact. By the end of the first year, I was headlining so it was going better than I could have hoped.

Agenda: You were the first openly lesbian comic ever to appear on television in 1991 on an episode of Sally Jesse Raphael entitled “Breaking the Lesbian Stereotype…Lesbians Who Don’t Look Like Lesbians.” Do you feel that stereotype has been completely broken since?

Westenhoefer: The typical lesbian stereotype has been broken, but it doesn’t matter who you are looking at as a comic, because everyone can be stereotyped when setting up a joke. When I was on the Sally Jesse show, the typical lesbian stereotype at the time was “angry lesbian” and I was brought on to show there were so many more sides to being a lesbian: we are models, comics, business women, etc.

Agenda: What can your audience expect from your current show?

Westenhoefer: The audience can expect to laugh. Each show is different because I feed off the audience a lot and what’s going on that day. I love performing at the Birchmere because it has consistently been a great show, due to the diversity of the D.C. audience. I performed a lot in D.C. at [the] beginning of my career, so I know what to expect of the audience.

Agenda: Your girlfriend Jennifer describes you as having a “lack of appropriate boundaries” and this is the inspiration for “Totally Inappropriate.” Can you elaborate on this?

Westenhoefer: Jennifer and her family were brought up so well mannered and I have always been the type to say what is exactly on my mind. It doesn’t matter what it may be about and I don’t really shy away from anything, which normally leaves Jennifer in a state of shock.

Agenda: Describe your involvement with “We Have to Stop Now.”

Westenhoefer: It’s such an amazing show! It started last season, and the second season is taped and finished. I play a therapist for two women who are therapists. It’s really sweet and funny and has been received very well. The second season has Meredith Baxter’s involvement, which we are so excited about. Meredith came out right after we were on the same cruise together. When I saw Meredith come out to Matt Lauer on “Today,” several of the things she said we had discussed while on the cruise together. I was so happy for her.

Agenda: You participated in a photo shoot for the NOH8 campaign. How did you find the experience? Do you feel the campaign is helping the cause?

Westenhoefer: It’s getting a lot of attention and taken on a life of its own. The NOH8 campaign is drawing people’s attention since it makes use of mainstream pop culture figures. Adam Bouska really is a genius and it’s unbelievable how much attention his work has drawn.

Agenda: Coming out is such a personal choice. When you see comics like Wanda Sykes, who wait until later in their career to do so, do you wish you had done the same thing or did you know it was the right time for you then?

Westenhoefer: I’ve never been in the closet, so there was no choice. I was an openly gay college student, starting the gay group on campus and things like that. It was never an option to be closeted for me but I do believe it’s a personal choice and it has to be right for the person.