I’m dating someone special. Her name is Pockets. Well, it’s not actually Pockets, but I like to call her that anyway. I met Pockets at the end of April at this trans pool (as in 🎱) night that I go to in downtown Boston every Wednesday. She came up to me and introduced herself and started asking me about work — my favorite subject 🙄. “I don’t really like to talk about work when I’m not there, since I spend so much of my life there already,” I replied. Smooth. She was a little taken aback, and the conversation fizzled a bit after that. So how did we end up together? Well, let me tell you about the power of lesbianism. 👩‍❤️‍👩

The next day I was scrolling through Bumble and saw her in my feed. She had swiped right on me previously and I hadn’t realized. When I met her the night before, I was having a rough night and wasn’t fully sober and didn’t realize I was being flirted with. It suddenly dawned on me. “Fuck. She was trying to be nice. And she was cute!” I thought. So, in an effort to salvage it, I swiped right back on her and DM’ed her: “Hey, sorry I was awkward last night. I was having an off night. Can I take you out for Bubble tea to make up for it?” (or something like that, I don’t have it installed anymore to quote perfectly okay? This is my word, and as such is beyond contestation.) Thankfully, she accepted. We talked over Bumble for a while, and the next day met for Bubbletea at my favorite spot, Happy Lemon.

I bought us tea, we walked and talked for..hours, maybe? It was a while. I was (read: am) enamored. The next day, we didn’t see each other, but we talked over text. That would be the last day for some time that we would go without seeing each other. And by some time, I mean I’m fairly certain that yesterday (July 25, 2024) while I was traveling in NYC that it was the first day I hadn’t seen her since that date in early May. (Lesbian hint 1).

We went on a date every. single. day. in May. She was living with her ex and me with mine, so neither of us could invite the other home. It was like high school all over again (not even including that I’m literally a few months into puberty round two.) We leaned into PDA and deemed ourselves “The Trans Menaces” as we would express our physical desire for the other by shoving passionately the other into a wall and making out with them relentlessly. We went to concerts. We went to movies. We went out for dinners. We went for walks that lasted for hours. It was incredible. After about a week of dates, I realized this wasn’t the casual thing I had been looking for. I was catching feelings. I let the others I had been chatting with over dating apps know that I met someone and was taking a break from dating apps. I wasn’t sure if I wanted to be poly or not. I was still figuring out my breakup with Leif and I was in no rush to add yet another layer of complexity. And, I had been pretty comfortable with monogamy overall for most of my life. Pockets and I had a talk, and we started dropping the ol’ girlfriend word with each other. It was special. It was (is) my first relationship as me, as Shiloh. (I was still going by Elly then, until early July, but coming out as trans is a nonlinear journey and I was already Shiloh then.)

An intermission: Leif and I had opened up our relationship in November of 2023, I think I’ve previously mentioned. I had been on dates since then with men and enbys (enbies?) as enby Elly. It was fine. After I came out as trans femme in January, I didn’t have any dates for a bit while Leif and I tried to figure some things out (a few hookups, still). But after Leif let me know he couldn’t make it work and our relationship formally ended in March, I started going on date-dates. I wasn’t looking for anything serious. I was fairly broken and was only on HRT for about a month. Things were messy. *I* was messy. I went on a date with a woman. It was lovely. I went on a date with an enby. Also lovely.

As I moved further away from masculinity (not that I was exactly a shining pillar of it before…), I had a desire to try dating men again. I had almost exclusively dated men in life before, and I was curious what it would be like to be in a straight relationship with a man. So, I figured I’d try it again, but as a woman this time around. HOLY FUCK WAS THAT A NIGHTMARISH HELLSCAPE. Cis-hetero-women, I am SO sorry for you. Ugh. I’m sure there are some great men out there, and I imagine 90% of them are trans masc. The other 10%, well, I think are probably my cishet male friends. Let’s just say that being in a het relationship was not my vibe. I wanted to feel pretty, and feminine, and I thought because I was so early in my transition that being with another woman might not work out well for that. I was afraid that I would feel insecure about myself and would constantly compare myself to them, or the other way around. I just wanted to exist and be a princess. I discovered that I was wrong. I can get that from women, and frankly I prefer it. Enter Pockets.

Pockets is feminine and also butch. She’s goth. She’s thoughtful and kind. She makes me laugh. She treats me well. She listens. She cooks (incredibly, I’ll add). She makes me feel so pretty and feminine, in ways I had never experienced. I feel affirmed in my identity every time she looks at me. I love how she makes me feel. I love how I feel when I’m with her and when I’m not I love missing her company. I love her.

Since we started dating, I’ve learned so much about myself, about women, about kinks (😅), about different types of relationships than I had been in before. Some of this is just part of my transition, and parts of this are directly because of her. I was 2.5 months into my HRT journey when we started dating. It’s been almost 3 months now since then. My whole identity, body, and mind feels like it’s changed so much in such a short period of time. It’s so odd to reflect on it. I truly feel like an entirely different person than I did just a year ago.

Four weeks into our relationship we took a road trip from Boston to Madison, WI. (Lesbian hint #2) It was so cute and we had so much fun! I showed her some places I lived in Chicago and introduced her to some friends in the area.

Before our return voyage, she took me to a very fancy restaurant she learned about in Top Chef (The Harvey House) and I took her to get some of the best cheese curds in Wisconsin, as well as a gross brandy old-fashioned. We stayed at the Governor’s Mansion Inn and in the morning before leaving for home, we walked down to Lake Mendota and took one of my favorite photos ever:

On the way back, we went through New York to see the falls, and I may have also met her parents 😅😅😅. You know, a perfectly normal thing to do at 4 weeks into a relationship (Lesbian hint #4).

Her parents were lovely. I enjoyed my time with them. Her parents and us did end up watching the first episode of Shameless. I had never seen it before, but let me tell you that if you haven’t, it is a choice of a show to make your gf watch with your parents just a couple hours after meeting them. I WAS SO EMBARRASSED THE WHOLE TIME ESPECIALLY THE SCENE WHERE THE MAN’S DAUGHTER WAS FUCKING SOME GUY IN THE KITCHEN WHEN DAD CAME HOME AND OMG WHY DID I HAVE TO WATCH THAT WITH THEM 😭😶‍🌫️😶‍🌫️😶‍🌫️

Anyway, it was fine and I was clearly the only one who was like “WHAT IS HAPPENING” and it might be from growing up in a catholic family but that was a wild trip. I was mortified at the time but I can’t help but to laugh about it now.

Since that road trip, we’ve gone two a couple concerts and another road trip to a romantic cabin an hour north of Montreal for the fourth of July. Pockets had gotten her very first passport so I suggested we make use of it by getting the hell out of the US for the holiday.

Later today we’ll be going on our third road trip in just under 3 months (Lesbian hint #5) to Vermont (Lesbian hint #6) where we’ve rented another cute cabin, and we’ll go to a water front concert in Burlington, visit the Cabot cheese factory (Lesbian hint #7-infinity), get a tour of Ben & Jerry’s, and go for a lovely hike up the tallest mountain in VT.

Oh, also I’m basically living with her at this point. I’m waiting for my new car to be built, but realistically I should have purchased a U-Haul.

That’s all for now folks. Keep it gay, keep it gay, keep it gay!