The 15 Days of Being Single

I am a serial monogamist.

For a long time, I treated this label like an insult, akin to being called “loser” “clingy” “codependent.” Then, over the years, I not only began to accept it, but began to embrace it. I started to feel like maybe this wasn’t a negative boxing, but a preprogramming in my DNA that leads me to nest with someone the minute I get naked with them. On my second date with my last girlfriend, which, I feel like I should add lasted 22 hours straight and resulted in the queerest, most u-hauly sleepover ever, I cheekily outed myself while driving her back from one of the bars we’d just left. “Serial monogamist, right here,” I said, laughing nervously. “Me too. Oh well.” We smiled, and the hidden context was clear— you may now pass GO, you may now move at lightening speed to your joint bank accounts, pet coparenting and adopted Chinese babies. The relationship took off from there in no time, and within a couple of months (okay, weeks really) I was madly, totally, head-over-heels, never-felt-this-before in love with this woman, who I’ll call Lauren. Everything was perfect. And our habits of serial monogamy not only felt acceptable, but felt like a positive.




My entire life (my entire queer life, that is) people would criticize me for leap-frogging from one relationship into another. “Take some time alone,” they’d say. “You need to be single.” These unsolicited comments from friends, family, the homeless guy down the street, or whoever felt like that had license to give me life advice, initially irritated me. I didn’t want to be single. Being single was boring. And lonely. In short, fuck that. And yet, part of me knew they weren’t wrong. But after a failed marriage that left me shaken and questioning my entire future, I welcomed love back in with open arms, relieved that I still had a shot at kids, a family, the white picket fence— the works. This last relationship represented all of that to me.

In true queer-fashion, I thought this was it. At 32, I’d left so many broken hearts in my wake that one girl even dedicated the song “Jar of Hearts” to me. I’d cheated. More than once. Way more than once, actually. And I’d managed to disregard any and all feelings that were not directly my own. In short, I’d spent the greater part of three decades being impossibly selfish. After the dissolution of my marriage, I thought I’d learned my lesson. I was crushed that I’d failed my wife— this amazing woman I’d sworn my life to— and by the time I met Lauren, I felt like I’d done all the growth I needed, and the stars were finally lining up for me.

But the stars do not work that way. It turns out, the stars are a cosmic bitch, actually. I thought I’d earned this relationship with all of the soul-searching I’d had to do after my divorce. Stars, fate, God, the universe, mother nature, Allah, spirits, whatever, didn’t give a single fuck about the work I’d done. After 7 months together, Lauren broke it off in what would turn out to be the most heartbreaking, life-altering ending of any relationship I’ve ever had. Those 7 months with her were spent with night after night in my bed, where she quickly took over at least one drawer, my entire laundry basked and part of my always-packed coat closet. We had plans. We were going to have kids. They were going to keep my name, although she would never change hers. We were going to move to the suburbs in the fall. I was happy— maybe even happier than I’ve ever been.

I’ve only really been broken up with once before. And that was five years ago, by a girl I dated for two months who really wasn’t my type and didn’t do a whole lot for me. When she left me for another girl, I was butt-hurt for about three seconds, and then promptly moved on. So breaking up with Lauren was jarring, to say the least. And why we broke up, I firmly choose to believe, comes down largely on the fact I have never been alone.

So why should any of you give a shit about my newfound aloneness? Because I know I’m not alone in this. And I hope someone out there can get something out of this without having to learn this lesson the hard way. I hope I can learn the lessons for you. I’ve spent the last 10 years in relationships. And today is my 15th day of being single.

I know that doesn’t sound like a lot to most of you. But if I really look back on it, 15 days is probably the longest I’ve ever been truly alone. There hasn’t been a time when I didn’t have a fall back after ending a relationship— usually an ex, or someone I could run back to that would fill the gap. Now, I have no one. The hearts I’ve broken have all healed and moved on to greener pastures, which, I am surprisingly happy about. Besides, I have no interest in reliving the past. Tinder, Bumble, and a bunch of other dating apps I didn’t even know existed have been downloaded to my phone, but I hardly use them. And when I do, they’re lack-luster and almost make me feel worse about being alone.

It’s only been 15 days, but they have been the 15 longest days of my life. I understand now, to a degree, what addicts go through with sobriety. I have, in fact, been a relationship addict my entire gay life. And now, I’m breaking that cycle. I’m collecting my 15 day chip.

In honor of the upcoming holiday, I will summarize it like this:

On the first day of being single, the bastard fates/universe/God/whatever gave to me a broken heart, a lot of crying, and convincing myself this couldn’t possibly be the end.

On the second day of being single, the bastard fates/universe/blah blah blah gave to me a few less tears, a little more hope, and the feeling that maybe, possibly, I might gain something from this mess.

On the ninth day of being single, all that shit above gave to me the sense that I actually do need to be alone. That I need to learn how to like myself enough without the help of others. That looking for constant validation from my relationships is wearing and exhausting, and until I am okay enough with me, I’m always going to be looking for that from someone else.

On the tenth day… a lot of anger. Like, a lot. Let’s just say I’m out one iPhone 7 which was casually tossed across the room in a fit of rage, resulting in a very expensive tempter tantrum.

On the fifteenth day of being single, this is what’s been given to me: the ability to self-care. Since I’ve been alone, I’ve purchased 4 new jackets (one of which is Burberry), a brand new iPhone X, a new tattoo, and just about anything else I felt like. My rule of thumb has been Buy Whatever Makes Me Feel Good. I have a good paying job, and if spending money is going to soothe some of my angst and provide some comfort, I figure it could be worse. I could be drowning myself in whiskey, sex, or worse. If a little credit card debt is the worst thing that comes out of this, I’ll count that as a win.

I’ve also learned something very important: I have people. I’ve reconnected with friends who I haven’t seen in ages, because I’ve been so wrapped up in my relationship. I’ve fortified new friendships. I’ve surrounded myself with people who love me, and appreciate me for who I am. And for the first time in my life, that has felt more than fulfilling.



Rely on people who have been there for you, even when you haven’t been (featured: my friend and coworker Rachel at our hospital holiday party last week)

I’m not going to sit here and tell all of you serial monogamists to please stand up, end your relationship, or stop looking for one, and travel down this road of loving yourself with me. It took me a decade to be ready for this, and even now, I had to be forced. I’m also not saying it’s easy. In fact, I’d dare say it’s the hardest thing I’ve ever done (and I’ve literally sliced into people’s rectums with scalpels). I struggle every day, every moment of every day really, to remind myself that I am good enough. That I don’t need to be desired or wanted or pined after to know that. And everyday it gets a little easier. I’ve learned to sit in the discomfort of being alone. The discomfort of not having that go-to person to text about your day. The silence from my cell phone (which has proven very unsettling at times). The terror of sleeping by myself. I’ve learned that Lauren breaking up with me was not because I wasn’t attractive enough, or smart enough, or interesting enough. It was because she simply couldn’t love me enough for both of us. But the hardest part has been reminding myself that, even if she did break up with me because I just wasn’t “the one,” that is not a reflection on the rest of my life.

So, if you, fellow serial monogamist queers, find yourself in this similar situation someday, know that there is good to come from it. There are lessons to be learned. The tears and the anger and the discomfort will give you the strength and the resilience to be better the next time, and, more importantly, to know there will be a next time. Even if that next time isn’t right now.


Holiday Party Style

December is almost over, but the holiday parties are just revving up. Stumped on how to pull off an outfit that’s dapper without trying too hard? Here are some of my suggestions.

The Leather Jacket


I love my leather jacket. No, really. I think it’s my favorite piece ever. It’s nothing fancy, but it fits perfectly. I’m sure I’ve mentioned it a million times before, but a leather jacket that doesn’t fit well looks sloppy and super 80’s. Mine is actually a Wilson’s Leather women’s small. If I had my way, I’d own a Schott leather jacket like this one (I’m obsessed… Someday, I’ll get one). But until I start making some bucks… I’ll continue to wear the hell out of this one. You should be able to zip the jacket up, and it should hit just ABOVE the belt. The body should be tight, and the sleeves should not be at all baggy. Once you get a jacket you love, you can pair it with literally anything, including a tie. This works especially well with a knit tie like this one from American Eagle.

Shirt- H&M

Jeans- Zara

Belt- H&M

Jacket- Wilson’s Leather

Tie- American Eagle


The Solid Bow Tie

I’m always hesitant to wear bow ties, for fear of looking like Jacob’s bar mitvah. But this looks actually works really well for a company party or a holiday concert. If you’re worried about looking infantile, like me, I’d suggest going with a simple, solid color (like the gray one here). Steer clear of crazy patterns and prints. Add some suspenders, but if you’re short, like I am, you’ll want to go with a thinner strap. Pair it with some skinny pants for a more modern look.

Tie- American Apparel

Suspenders- Ebay

Pants- Zara




A Dapper Butch (DykeNight-Boston) Event!

I just wanted to give everyone a heads up about a great event that’s happening in Boston on December 19th!

The ladies at Dyke Night Boston will be hosting a fantastic 21+ queer dating event at Urban Art Bar- 709 E. Broadway, Boston, on 12/16 at 7pm!

I’ll be reading from my new book, Searching for Forever,  to get the party started. I encourage any and all ladies (single or taken) to come check this out.

“No this is not speed dating!!! Think of this as a giant card game. Everyone is going to be given a card with some clues and a unique fact about themselves. Groups will then whittle down to 6 people that will be matched at random and then the games will really begin as people sit down as a table of 6 strangers for the 2nd part of the event. We can’t give way any more secrets, sign up with friends, or solo and meet a new significant other or a new life friend!”


Register here (only $10!)! But hurry! It’s filling up!



The Art of Layering…Part II





The Old Standard

Some things will never go out of a style. And a peacoat is one of them. I’ve been wearing one since I was 15, and my grandfather and his Navy buddies wore them long before that. Wall Street boys wear them. Steve McQueen wore them. They’re timeless. And you can do it with just about anything. Try pairing your old peacoat with a chambray shirt, tie and cardigan, like I did here. I also threw in a pair of distressed jeans from All Saints to keep things more casual (it is Friday, after all).






















































Pro tip: Get a pair of these brogue boots. They’re brogues… but they’re also boots. Get it?! No but really, these things are amazing. The white soul make them casual enough to wear with jeans, but the wingtip stitching and chocolate brown leather makes them dressy enough for a suit.


These came from American Eagle, believe it or not.

Vests: They Aren’t Just for the Woods Anymore


























One of my favorite looks right now is a vest over a suit. I know it sounds funny, but trust me. It looks amazing. Put on your favorite suit and top it off with a matte, down vest, like this one with color blocking and gray flannel. Bonus points if it has tweed on it (I just couldn’t find one in my size).



The Toggle Sweater

I love everything toggle… Sweaters, coats… Okay, well maybe that’s it. But still, I love it. Toggle buttons hold this weird juxtaposition of sophistication and Paddington Bear that just really does it for me. Find a good, chunky toggle sweater like this one from H&M, and you can wear it like a jacket, or layer it under a long driving coat like I did. This driving coat is my new favorite, by the way. It’s almost impossible for me to find a long coat that doesn’t come down to my ankles. This Zara boy’s find was a steal. Not the warmest thing ever, but it sure does look great over a heavy sweater.