March 29, 2024 | B.J. Daniels

Debi Vance and Cindy Olsheske: the dynamic duo

Together nearly 45 years, the couple has defined LGBTQ community involvement for decades.

Debi Vance and Cindy Olsheske

Debi Vance knew early on in her childhood that she was different. She was a tomboy and a fighter.

As her identity became clear she developed a sense of community involvement from early LGBTQ+ leaders and friends like Si Smits (Boot Camp.) Bob Schmidt (M&M Club,) Wayne Bernhagen (Wreck Room,) Chuck Cicerello (The Factory,) and Tony Canfora (Club 219.)

Cindy Olsheske, her life partner of 44 years, grew up living a lovely suburban family lifestyle. She had no great “aha” moment that she was a lesbian. She always had the support of lots of family and friends. She found a career and social life mentor in Michael Nelson.

The very first gay bar Cindy remembers is This Is It, where all the “chapettes” (people who worked at Chapman's Department Store like she did) gathered for happy hour. Meanwhile, Debi went to the flash-in-the-pan hotspot The Red Baron, which was known for its live concerts, including Grace Jones in 1979. Debi became one of the few female bartenders at mostly male gay establishments, including M&M Club and Club 219.

Together they became powerhouses in the Milwaukee LGBTQ community. Through volunteering and attending community events, they met many city, state and national leaders. Some of their favorite memories were brought about by their dedication to and participation in the numerous sports leagues that became prevalent in the LGBTQ scene of the 1980s.

Debi and Cindy feel that gay people helped each other more, and shared a lot more camaraderie in the past, through the volunteer efforts they participated in.

A lifetime of service

They became heavy hitters (pun intended) in the MGSN (Milwaukee Gay Sports Network), HIT (Holiday Invitational Bowling Tournament), SSBL (Saturday Softball League), MilMaids (Milwaukee Madison Against AIDS), Investment Club, and the Cream City Chorus. They performed many roles for these organizations including sitting on the board of directors and coaching softball teams like the M&M Peanuts. Along the way, they attended tournaments across the nation.

Their annual “Milwaukee invades Acapulco” trips with the M&M crew became the stuff of legend. Debi also attended the National March on Washington for Lesbian and Gay Rights in October 1979. She traveled by train to Washington, D.C. with Miss Ann.

Debi and Cindy are most proud of their long-standing commitment to MilMaids, short for Milwaukee Madison Against AIDS, and a charitable 9 PIN-Bowling Tournament that was started in 1985 in response to the AIDS crisis.

Debi Vance and Cindy Olsheske

The tournament alternates between Madison and Milwaukee each year. All proceeds benefit a local HIV/AIDS service organization. This year's beneficiary is the Holton Street Clinic.

Debi and Cindy have been actively involved with MilMaids for 35 years.

Cindy is also proud of organizing the very first AIDS fundraiser in Grand Rapids, Michigan.

In 2020, Debi Vance received an LGBTQ Progress Award from the Shepherd Express for a lifetime of community service.

Closing thoughts

Debi and Cindy are both very concerned that the rights that their generation fought so hard for are being eroded and reversed.

They implore everyone to VOTE like your life depends on it.

Their words of advice to the LGBTQ youth of today are, “Be yourself, be respectful -- and get involved!"