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But I figured I still had time. Other elements of lesbian culture have been steadily dying ; why should Olivia be any different? As I walked around the ship, which holds over 2, passengers, it was already clear that the average woman here was a couple decades older than me. We all formed one big circle, and the staffers got the ball rolling.

First things first: How had we all heard about Olivia? Now Jamie was back for her second Olivia cruise with her partner Matie, who runs Self Serve , a sexuality resource center and sex shop in Albuquerque, New Mexico; their other partner was stuck at home, studying for exams. It became this…spiritual experience, almost. To see all these older pairs of hands holding each other — it was so beautiful and safe.

The Friend Zone - Anwar Jibawi

After everyone had doled out sufficient praise for the company, the conversation quickly turned, in perhaps inevitable millennial fashion, to everything Olivia could be doing a better job of when it comes to attracting a younger generation of queers. Some people suggested that Olivia offer scholarships or student discounts, since cruising is so expensive. Someone mentioned that they were surprised there were no sex toys available for sale on board.

Later in the week, Tisha Floratos, the vice president of travel for Olivia, told me that she and her staff think about this a lot. Maybe Olivia could do a specific queer-plus trip for trans people and gay men? The room exploded. Judy had to come up with all the money up front — she convinced women from around the country to put down deposits a full year ahead of time, with no real guarantee that the ship would ever sail — but it sold out nearly immediately.

Judy and Rachel chartered a second boat, and Olivia Travel was born. Nor did we want to dismiss the radical potential of dyke spaces. I actively choose to identify as a lesbian and a dyke, as well as a queer.

More Friends to Lovers

Meanwhile, lesbian activist groups like the Lesbian Avengers have been pro-trans for decades. But there were, in fact, a number of stereotype-fulfilling boomer TERFs on board the cruise — and plenty of lesbians whose policing of gender norms took more banal forms. The woman who bought me a drink after I sang Kelly Clarkson at karaoke — a petite therapist from California with a prim gray bob — ended up being one of them. Throughout the trip, Matie and Jamie would have a number of tearful conversations about trans inclusion with some older passengers who refused to accept trans women as their fellow sisters.

But they also got many women to reconsider their more middle-of-the-road views on trans inclusion. A couple days later — after getting my serious lesbian conversations out of the way — I was about 14 rum punches deep and drunk-dancing on a catamaran. Whenever we docked at port, we were offered a bunch of different excursions vetted by Celebrity and Olivia, and Dana had generously offered to book one for me.

Kitts to the island of Nevis instead. Ugh, fine , if I must. At first, sitting alone on the catamaran heading out for my snorkeling excursion, I felt shy again, and wished I had Dana or Jamie and Matie at my side. One of the guys running the boat, a youngish dude with dreads, took pity on me and brought me a glass of water. He asked me if I was staff on the cruise, noting my friendlessness, and I told him I was a reporter.


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But he did occasionally seem to forget about the realities of the situation. For the last stretch of our afternoon, we were dropped on a secluded beach at Nevis, where a few of us ferried beers and our new favorite drink, the very college-esque Panty Ripper coconut rum and pineapple juice , from shore to the rest of the women waiting in the water.

One woman stuffed a bunch of beers into her bathing suit and we cheered whenever anybody pulled one out. A couple women had GoPro cameras, with which we took a lot of increasingly drunken group shots while we swam. One of them was attached to a floating handle that looked very much like a big yellow dildo, which, once somebody pointed it out, kept sending us into hysterics. Bonding is built into an Olivia trip, which, I realized soon enough, is basically like grown-up lesbian camp. On this floating gay island and its satellite getaways, time works differently than it does back home.

You can skip the normal-life process of slowly getting to know somebody on the shallowest of levels and get right to the good stuff. Back on the catamaran for our return to port, we got into some deep and very lesbian-y talk about relationships. In the spirit of lesbian camp bonding, I told my new crew about my situation — nonmonogamous, not sure how to feel about it — which seemed to pique the interest of beer bathing suit girl, because she would soon afterward follow me into the impossibly tiny bathroom, bursting in on me mid-pee.


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By this point, I was — somewhat unintentionally — quite drunk. But there was another part of me that was very much not into it, especially when the makeout gave way to other things and people started banging on the bathroom door. I was also, literally, developing a pretty bad sunburn.

I made my way up the tiny laddered chute to the deck, bouncing against the walls like a pinball, and immediately moved as far away from the bathroom as possible. Later, when telling friends what had happened, I did laugh about it — one told me it sounded like something pulled straight out of The L Word , which, true — but I was also a little mad at that girl, and even more so at myself for being so sloppy.

The consent element there was indeterminate; I had willingly gone along with the hookup, at least for a little while, though I remain uncertain about how much I really could have consented while drunk-peeing in a bathroom the size of a broom closet.

The Time I Went On A Lesbian Cruise And It Blew Up My Entire Life

Bad sex happens. Even with lesbians! I was going to move on, get over it, and go back to enjoying myself. Before I left, I talked to a few of my reporter friends about it, just in case a hookup opportunity should present itself and I decided to partake for, um, research purposes. We decided that my Olivia story fell in some sort of weird journalistic in-between, just like my own job does.

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And the thing a lot of women on the cruise were looking to experience was, yes, getting laid. Instead, I found singles and couples of various ages and gender presentations looking for something extra, something different, something more. My lesbian friends and I have often complained about how much easier it is for our gay guy friends to hook up with abandon — they have way more bars, and they all have back rooms!

On Grindr, you can just ask someone to skip right to the sex. That is, in fact, the norm. One of my friends was in a hot tub, in the middle of the day, when she noticed that the women across from her were having sex in the same hot tub she got out immediately. My friends Jamie and Matie, for their part, were determined to make things happen. At our evening activities, Jamie was frequently flagging , via colored handkerchiefs placed in her back pocket. She and Matie also hung up a white board outside their door and encouraged their neighbors to invite them to their play parties.

They had a very sweet exchange with a curious anonymous neighbor who wrote them a note, inquiring what a play party is. It was only on our last day at sea that I discovered a Public Posts board, tucked away by reception in an area that most guests definitely would not be walking by every day.

Afterward, I had lunch with Dana and some of the other Olivia staffers and asked them about it — why not make the Public Posts more prominent, MichFest style? Especially since the younger people at the first Gen O event had explicitly asked for more sex content. Olivia had run sexuality and intimacy workshops before, and at the lunch, the staffers floated the definite possibility that they will again.

Christmas with the Billionaire

Tisha, the cruise director and VP, met her wife on an Olivia cruise. When my partner jokingly warned me, before I left for the cruise, not to fall in love with a hot older butch — seriously, we joked about this — I thought, Fat chance. Not only because I had no intention of falling in love with anyone else, but because I thought hooking up with hot older butches would remain the stuff of my fantasies. I even reported out an entire article about intergenerational lesbian relationships a few years ago. I have a lot to share.