Chatting up Kelli Carpenter

As she rejoices in her family, her thriving business, and finding love again.


Photo By: Geraldine McBrearty

We know Kelli Carpenter because of her relationship with celebrity powerhouse Rosie O’Donnell, but there is more to the whip-smart blonde than all the star-centric media coverage would have us believe. In the late 1990s, Carpenter was a welcome addition to the lesbian limelight when our eyes were glued to the tabloids for news of Ellen, k.d. and Melissa, but she has always had her own unique story. Now, for the first time, Carpenter tells that story, and lets us in on what she’s been doing since the 2007 separation from the woman who made her famous.

Kelli Carpenter appeared on our radar in the heyday of lesbian chic, at a time when we looked at a handful of famous lesbians as test cases for our own acceptance: If this select group of women could come out on TV, get married, be invited to the White House, have children, then perhaps we, too, would find happiness. Because if they couldn’t, how could we? As it turns out, Carpenter did find happiness, then heartbreak and eventually happiness again—just like the rest of us. Along the way, she has reconnected with her roots and learned to touch her own life again. This self-described Ragin’ Cajun from Baton Rouge, La., is currently residing in New York and devoting her energies to her fiancée, the four kids she shares custody of with O’Donnell, and her business, R Family Vacations.

As a closeted college student in the South, Carpenter learned to balance her own truth against the expectations of others, especially those of her very religious family, who would not accept her sexuality. She knew she was gay on day one of junior high, but she stayed in the closet, and in college she even had a fake boyfriend, who was also gay. “We had ’em all fooled,” she laughs wryly. “We went to every sorority-fraternity party—then we went to the gay bars afterwards.” Her parents, however, were not amused. They insisted that she attend Homosexuals Anonymous (HA) meetings in exchange for her college tuition. “I had the wherewithal to think, ‘It’s only four years of my life, and once I graduate from college I’m going to get a job, and I can just say goodbye.’ ”

Certain of her sexuality, and that there was nothing aberrant about it, Carpenter was dispirited by the meetings, where she observed “an assortment of people who were sad in their lives, but it really had nothing to do with being gay.” 

Needless to say, Carpenter was relieved and happy when she got her degree in advertising and launched her life as an independent adult. Attracted to the energy and pace of the advertising world, its focus on creativity and the bottom line, Carpenter began to succeed quickly, first working with an ad agency on the Pepsi-Cola account, then Kellogg’s, which led to her being hired as marketing director at Nickelodeon. Mostly run by women, Nickelodeon was a creative and democratic company, and Carpenter felt comfortable in that environment. “There was not a day when I didn’t wake up and love going to work,” she says. In just a few years she had moved from Texas to Chicago to New York City, where she had always dreamed of living.

It was 1996, and queer culture was blossoming. Thirty years old and single, Carpenter socialized with lesbian work colleagues and dated women. Then, in 1997, the same year Ellen DeGeneres came out, Carpenter found herself in the orbit of talk show host Rosie O’Donnell.  O’Donnell’s brother, Daniel, set the women up on a blind date and after that it was full speed ahead. “I ended up with two kids and a big relationship very quickly,” says Carpenter. “It’s like being thrown into a tidal wave,” she says of her life with a celebrity. “I was happy with the success I had created in my own little world, before it was hit by the tidal wave,” she laughs.

“In the very beginning, it was overwhelming. Everybody was taken into the public eye with my choices. It was a lot, but we all survived and it found its balance.” Carpenter kept her job at Nickelodeon for a year, which gave her a day-to-day routine that was her own, but eventually, family life began to dominate and she became the first lesbian celebrity instamom. 

Parker was 2 and Chelsea was a newborn when Carpenter met Rosie, and as kid-friendly as she was, the ambitious ad exec had never even changed a diaper before. “I remember walking in and somebody said to me, ‘Can you just change her diaper before we leave?’ And I was like, Yeah, sure, no problem, how hard can it be? I knew I wanted to be a mom but it was an interesting way to walk into it, because it’s not like you start from day one.”

At the time, lesbians having or adopting babies was a novelty and the constant press coverage turned a tidal wave into a tsunami. “The media was always sort of mad at Ro for not coming out until the time she did. The sad part was that this was the only part of our lives that felt private. We were real trailblazers in the [lesbian parenting] arena. I mean, Parker’s 17 years old now.”


Pictured: Kelli Carpenter and family, Photo By: Geraldine McBrearty


Next, O’Donnell and Carpenter adopted Blake at birth, and then Carpenter gave birth to their fourth child, Vivienne, through artificial insemination. In this gay family, marriage came after love and the baby carriage: O’Donnell and Carpenter took their vows in San Francisco in 2004, two weeks after gay marriage passed into law. “I look back and when I think about the initiating reasons, it’s not that we ever chose not to get married, it just never really came up. And when we saw what was happening in San Francisco, we said, ‘You know what, we have children, we should be out there, we should do it.’ It was a very quick decision—and maybe the initial motivation wasn’t the vows and getting married. However, when we took the vows, it felt very powerful and meaningful at the time. I think both of us took those vows very seriously.” 

In spite of their commitment to each other, eventually the relationship was in trouble. She does not want to dwell on what went wrong, because it was no different, she believes, from the experience of any painful breakup. What Carpenter really wants to convey is how she got past the heartbreak, to “touch her own life again.

“I now look at relationships completely differently. I think that over the course of a long period of time people change. I look at people who have been in relationships for 30, 40, 50 years. I think that they change and are still compatible.

“There was no one thing that I would put my finger on that was the beginning of the end. I think it’s a series of things that happened—that once it started to go, there was no real salvation for it. The hard part was that we had children, and there was a lot of sadness involved, much hurt and broken promises. Truthfully, once you come out of the dark place, there is the opportunity for change and healing. I’m happy now, [Rosie’s] happy now, the kids are really good and very happy. You can find the ability to move forward, even though in the moment you feel like you’re never going to crawl out of that hole.”

Gregg Kaminsky, who is Carpenter’s business partner and friend, offered his support. “When they were going through rough times, I was certainly there for Kelli, to have someone she could confide in. I am there for her 24/7, as she is for me. Kelli is a very strong person, so I always knew things would eventually work out.”

And they did, eventually. “There was a lot of back-and-forth,” reflects Carpenter. “Both sides did the most we each could to make it work. It took a year. It was incredibly painful.”

She had become too thin, was run down and anxious. Over the course of 12 years, she had lost her sense of self, apart from her status as wife and mother. She felt unable to focus and was on medication for depression and anxiety.

“At some point I just said, ‘I’ve got to find a healthier way to get through this,’ and stumbled upon a Buddhist meditation center, which, truthfully—beyond therapy, beyond drugs—completely changed my way of thinking. Just the idea that any situation is tolerable, it’s just a matter of how you think about it—I just found that so empowering.

“With pain comes wisdom. I have lived a very blessed life, without huge amounts of pain involved. [But] I think that having significant incidents of bring-me-to-my-knees moments really changed my life.”


Pictured: Kelli Carpenter, Photo By: Geraldine McBrearty


What changed for Carpenter was that she regained her sense of self, her regular life. “I have such amazing memories that I wouldn’t trade for anything, but who I am now—I am very content with the normalcy of my day-to-day existence. I think I lost touch with what drives me.”

One of the things that drives Carpenter is business, and R Family Vacations is her main focus now. “It really is just wonderful to see the community growing. When I think back on high school, and the torment I felt about being gay and not being able to have a family—kids today just don’t feel that.”

In addition to R Family Vacations, Carpenter and Kaminsky have expanded their brand to include adult-only trips that cater to the LGBT community. “We have found that our guests include a significant number of gay and lesbian travelers who are looking to travel together, and not just with all men or all women.  To date, we are the only company providing this opportunity, and we are very excited about its growth potential,” says Carpenter. They have also diversified their portfolio of trips to include a Broadway cruise, offering the ultimate vacation for Broadway theater-lovers. 

And Kaminsky shares Carpenter’s enthusiasm. “We have diversified and expanded in the past couple of years and next year have an exciting lineup that includes trips to Vegas, France, Mexico, Spain, the Berkshire Mountains and California.” 

But he is also excited for Kelli’s personal life. “Kelli is engaged to a beautiful and talented woman who we have both known for many years, because she has performed often on the R Family trips. Kelli is very happy and peaceful, and she continues to be a wonderful mother to her four children and an enthusiastic business partner and incredible friend.”

So, who is that svelte redhead who’s now filling Carpenter’s heart with love? It’s Anne Steele, an award-winning cabaret singer. Their future together was merely a speck on the horizon until fate intervened on the high seas. 

“A couple of years ago we were both on a trip, and we both happened to be single, and all of a sudden she was sitting next to me and I was like, ‘It’s Anne!,’ ” says Carpenter, her eyes twinkling with the memory. “And we started talking and flirting and my heart was racing and my hands were sweating and it just sort of happened. I couldn’t believe it. Still, even to this day, I just look at her and think, ‘It’s Anne!’ I can’t believe it.”

Carpenter’s heart might have been racing, but her head was proceeding with caution. “My kids knew her from the trips and they really loved her, and I didn’t want them to know that we were dating until I was sure she was somebody I wanted to date long-term. They had been through so much already. I waited eight months and then told them, and they were like, fists in the air, ‘Yay!’ They love her. She loves them. It’s a joy I can’t even express.”  

“With Anne in my life, and my parents completely involved in our kids’ lives, I feel a sense of peace within my family that I never thought possible. Life is really good right now.”


Lezzie Lightning Round With Kelli Carpenter

On how R Family Vacations began: I took the kids to Provincetown for Family Week, and it was beautiful to watch the kids looking around and saying, “Wait, those kids have two mommies, too!” And feeling a sense of community that children with gay parents usually do not feel on a day-to-day basis. So we decided to give it a shot. I thought that if my kids, who have access to so much in life, are longing for it, then the kids in the middle of Idaho or Mississippi—those families who don’t have any sense of community—we could create something that could give them that.

How it gets better: These kids are able to meet other families and fill up their self-esteem over their vacation. They absorb all the love and the acceptance and community—everything that they’ve been longing for all year. It helps them go back into their world, until next year. Over time, the company has grown. We’ll have a family of 10 book, and maybe only one couple is gay, but they’ll bring their brother and sister, who have two kids, and their parents, and their aunts and uncles, and all of a sudden we’ve got a reflection of what the real world looks like, or what we wish the real world looked like.

On life now: [Rosie and I] were meant to have that time together, and beautiful kids, but we were also not meant to be together for this second half. [R Family Vacations] has become less about celebrity and more about community. The trips are more about people searching for friends, and talking and engaging, being present and enjoying the moment that they’re in. When a celebrity comes out, it somehow makes us all feel better, but it doesn’t mean real acceptance—that we’ve achieved the things we’re fighting for. I think as a community we need to find it within ourselves as everyday people to go out and fight for what it is that we deserve.

On marrying again: Anne and I are engaged to be married next summer. I am grateful for each day we share together and feel so blessed to have her in not only my life but the kids’ lives, too.

What she’d most like to be remembered for: For the business that Gregg and I have created. It’s new, it’s unique, and it’s important for the gay teens of today to know that creating families is an option. Gay families can also help change the right-wing Republican viewpoint of what the “gay lifestyle” is. You could not bring a conservative Republican on our ship and not have their heart changed. That’s what I’d like to be known for—rather than as somebody’s ex. That, and for being a good mom. 

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