I Had a Baby with My Gay Best Friends

Kitty Stillufsen opens up about how she used her two best male pals — and a baster — to conceive her daughter.

2 Men, 1 Woman & a Baby
(Image credit: Ali Smith/alismith.com)

I'd already been through 10 hours of intense labor with no sleep when my friends Darren and Sam breezed into the delivery room. I took one look at them in their Members Only jackets, bagels and coffees in hand, huge smiles on their faces, and ordered them out. (I remember managing an "Okyouguyscannotbehererightnow

soiwillseeyoulaterbye!" Darren describes a scene more akin to The Exorcist, where my head turned completely around and a nonhuman voice commanded them to "Get. Out. Now!"). Still, they stuck around for another 10 grueling hours, until I gave birth by C-section. I was pretty out of it, but I overheard Darren talking to the nurse who'd folded out the "daddy chair" into a "daddy bed" and put a little toothbrush-and-soap overnight kit on it. "We're going to need two of those," he told her. The nurse gave him a look of utter confusion; then, once he explained, she kindly obliged. We needed two daddy beds, he told her, because the baby has two daddies.

At 38 years old, I've been lucky in my life. I run Red's, a successful lobster restaurant on the Jersey Shore, with my family and spend winters surfing and teaching yoga in Costa Rica, where I have a great group of friends. By the time I was 33, I'd pretty much done everything on my to-do list — traveled, carved out a career, bought two homes, and had a lot of fun. I'd also married a controlling and demeaning man. After eight years, it became unbearable, and when I kicked him out of my house and filed for divorce four years ago, I felt empowered and free. But I wanted a family. I knew I had too much love in my heart not to have a baby, and I believed it was important that the child have a great dad. About a year after my marriage ended, I was dating a prince of a guy who wasn't ready for a family — and the pressure he felt from me to have a baby ultimately broke us up. It was around then that I started joking with my best friend, Darren, about what great parents we'd make together.

I met Darren Greenblatt 20 years ago as a freshman in college, and it was love at first sight. We had identical, self-deprecating senses of humor and a mutual love of mischief. We scammed our way onto the lists of New York City nightclubs and went on wild shopping escapades all over town. We also shared strong notions of right and wrong and a drive to be successful in life. Darren — now a fashion industry consultant in New York City — is loyal, kind, fun, generous, talented, and smart. After all this time, he knows me better than I know myself, and he'd be the perfect boyfriend, except that he already has the perfect boyfriend. For six years he's been with Sam, a sexy, brainy guy who teaches French and African history at a prep school.

One day in the fall of 2006, we were in a lingerie shop where Darren and Sam were helping me find some sexy underwear for a date. In a total I-love-you-guys moment, I blurted out, "You two would be the best dads! When are we going to have a baby together?" We all laughed. And then we stopped laughing. It was too crazy to consider — can you imagine us all raising a child together? But as the months went on, the idea kept coming up, and our conversations about it got serious.

We spent a good year discussing it — whether we could afford it, what would happen if I moved to Costa Rica full time, or if their jobs took them away, or if, God forbid, Sam and Darren were to break up. I'm convinced we talked about having a baby more than any regular couple ever did. Ultimately, we decided that life is unpredictable, so we'd just have to roll with whatever came up, like all parents do.

By Easter of 2007, we'd made our decision. The baby would have my egg, Darren's sperm, and Sam's last name. We wrote up a custody strategy with the help of some lawyer friends: I'd have the child with me in Costa Rica and the guys would visit us there, then when I was back we'd all split time between New York (where they live) and New Jersey (where I live).

Because I was past the prime baby-making years, I saw a fertility specialist, who told me everything was in order. It would cost more than 10 grand to be artificially inseminated, so we figured we'd first try to do it ourselves. Sex was out of the question (it would be like sleeping with your brother), so we tried the next best thing: the turkey baster. I bought a digital ovulation monitor, and during my first fertility window, we nailed the sequence in Sam and Darren's apartment: Darren did his thing in their bedroom, Sam ran it into the guest room where I was waiting. After he left, I sucked up the goods into the baster, did my thing, called out "OK!", and the guys came in and we gossiped for 20 minutes. The second month we tried it, I got pregnant.

I was selective about whom I told. Being in the service industry for so many years has made me good at reading people — I knew who could handle the full explanation and who couldn't. Most of our friends and family are progressive, so the response was pretty positive. Darren's parents and mine pledged their support and energy. But Sam's mother and stepfather, devout Evangelical Christians from Little Rock, Arkansas, had a harder time with it. They believe homosexuality is a sin and spend a good deal of time praying for our souls. But they ultimately came to acknowledge our baby as their grandchild, sending gifts and loving notes — which I find admirable. I was less impressed with a few of the guys' friends in the city, who weren't as supportive as we thought they'd be; they said it would never work out and told Darren and Sam to "get everything in writing."

A major challenge was choosing a name. We all wanted something retro and easy to remember but still unusual. But we had so many name associations between the three of us — anyone we'd dated, any wisecracking student Sam had taught — that agreeing was not easy. The guys bought every baby-name book ever published and made dozens of lists. Finally, we picked Olive Sophia. She was born in June 2009.

That first summer it was all hands on deck. Darren's mom stayed with me after I got home from the hospital — his folks have been power grandparents since, helping constantly — and the guys, who have summers off, were always around. I had to get back to work immediately because it was high season at the restaurant, but we all got on a baby schedule and we made it work. Actually, Darren and Sam made it fun. Every new mom should have a gay couple around: They saw me at my worst — leaky breasts, writhing in pain, sleep-deprived and delirious after being up all night with the baby — and they told me constantly how beautiful I was. They bought me comfy pajamas for after the delivery and cute lingerie for when I started to get my body back. They sent out birth announcements, made a detailed list of who gave gifts, and mailed all the thank-you notes without my having to lift a finger. I have friends whose baby-daddies are involved parents, and plenty whose aren't. Most of the time, Sam and Darren are like two doting, energetic, organized husbands. They also provide financial support — it's not as structured as a check every week, but they contribute to buying diapers, food, clothes, and other expenses for Olive. Big expenses, like college, we'll split three ways.

Winters are mommy-and-Olive time in Costa Rica, summers include a lot of daddies-and-Olive time (since I work a lot), and in between, we see her equally. Sam and Darren rent a house in my New Jersey town, Point Pleasant Beach, and I come in to Manhattan regularly. So far, they've seen her even more than we'd planned — usually staying overnight during "the handoff."

But we have our rough patches. In the summer, I'm at the restaurant, slaving around the clock — whether it's planning food orders, updating our Facebook page, or dealing with our 40 employees — while Darren's parents or family friends watch Olive. Meanwhile, Darren and Sam have demanding jobs in Manhattan, so sometimes it's hard for them to get out to Jersey when I need them, and I'm like, "This is your commitment. Make time!"

There are days when I feel like a working single mom, and I don't think the boys always get how hard that is. A family friend of mine — I'll call her Aunt Lilly — watches Olive three times a week when I'm working. Aunt Lilly's an angel — she managed to get Olive on a sleep schedule when I couldn't. One day, Lilly bought some packaged Chef Boyardee meals for Olive. Sam, Darren, and I eat healthy and organic, so when the guys caught wind that their daughter ate canned noodles, they hit the panic button and said it was "worth having a conversation" with Aunt Lilly. I was like, "Dudes, Aunt Lilly is my lifeline. She can feed Olive pepperoni pizza coated in refined sugar and lard for all I care as long as she keeps coming over!" You have these lofty plans for the baby, and then reality sets in and you're ordering Domino's and just surviving! The boys got it instantly — but it'll be interesting to see what happens when we get to the point of deciding whether teenaged Olive can have a boyfriend sleep over.

As for my dating life, I thought it would be an issue, that my being a single mom would send the men running. But beyond the scheduling challenges, my romantic life has been surprisingly good. Lots of women my age have children with exes they hate, so the fact that I love Olive's dads and they're involved in her life is refreshing to guys, and it takes some of the pressure off them. Working Olive's "fathers" into first-date conversations has earned me a few double takes, though.

And Olive will also face the challenge of having to explain her family. People ask me presumptuous questions about the custody agreement or whether her daddies play an active role or if I just asked my gay best friend for his sperm. That couldn't be further from the truth. Darren, Sam, Olive, and I — we're a family. We're the real thing. I know we'll face challenges that a regular family wouldn't. But while plenty of married couples make great parents, some don't! I'm just happy that my daughter has a mommy and two daddies who all love each other, and are bananas about her.

I'm not a sappy person (that's Sam's specialty), but I choke up a little when I think back to a moment that repeated itself a lot last winter, Olive's first in Costa Rica. I'd get her ready for bed, make sure she had a big bottle, and lie with her in the hammock on the porch, rocking gently and singing to her until she fell asleep. Sitting there in the blackest dark, surrounded by the beating of the waves and the night sounds, I'd hear Olive's breathing, and I'd pull her close and think, Wow, I did it. And I'd feel deeply grateful for the family that I've been lucky enough to create for my daughter. I couldn't imagine a better one.