DISCLAIMER: This post is going to discuss my recent dating life, and some pretty scandalous things guys on OKCupid have requested I do. Read at your own risk, especially if you’re family.

I’ve been trying to write this post for a couple of months now, and have never quite known how to start or where it was going to end up.

But here goes nothing.

It’s been over a year since I moved out of my home I had made in Chicago with my wife after learning about my divorce.

It was such a journey. I was jaded and heartbroken, and thought that getting close to people can only end badly.

Perhaps that’s still the case, but I decided to take the plunge.

I’ve begun dating again.

It’s pretty jarring when you get used to the fact that you’re going to be with one person for the rest of your life, only to realize you’re once again single at age 30, and, paired with a new job and moving halfway across the country to a town in which I knew no one, it took some adjusting.

I joined Tinder around the time I moved to Delaware last November, mainly because I was so desperate for any sort of human connection…but at that time, ideally platonic. I was an absolute mess, and in no state to be able to “date” anyone. Which, to be fair, isn’t exactly what Tinder advertises. But Tinder wasn’t around the last time I was single, so I was curious. But I poked around there and vaguely talked with a couple people, which never led to anything. It was probably for the best.

I spent the winter rediscovering myself, without the pressures of school, without a romantic partner.  Just me. Figuring out what I was all about, as an adult. Unearthing myself from the rubble of depression and a broken marriage. Though I missed the…comfortableness…of a partner. Someone to come home to. Someone to witness my life along with me. But I needed this time and forced myself to stare at my singlehood head-on. Figure out where I was, and where I wanted to go in life.

I really had no idea, to be honest. I sometimes thought, “What’s the point in dating again, anyway? It either ends badly or you end up together for forever. And, half the time when you think you’re going to end up together forever, it turns out to be a lie anyway.” The odds are not in our favor. Was it even worth it for me to go down this road again?

Yeah, I’m young. 30 and single. Of course I wasn’t really going to give up the prospect of dating and/or love up for the rest of my life, but, at that point, I didn’t see anything of consequence in my future any time soon.

Around this March or April, though, the idea of “dipping my toes back into the dating pool” began to interest me. But that was right before I was going to leave for two months for my summer job, so I kinda tabled that thought. If something were to happen at “opera camp,” I was down, but that sort of stuff can get tricky too. Costume shops are a gossip mill, and the theatre community is a small and incestuous one.

I checked out the Tinder options in the area, to be honest, mostly to see how many of my coworkers’ profiles I could find. (If you were my coworker and you were a queer woman or straight man between the ages of 19 and 45 on Tinder, I totally saw your profile! #creeper)

Because it wasn’t my year-round home, I wasn’t very invested in meeting any of “the locals”, just in case I ended up getting too attached. Of course, the general demographic was the deer-hunting farm boys (soooooo not my type) so this wasn’t a problem for me. But, as a fluke, I met a cool dude on Tinder this June and went on my first “first date” in nearly 5 years, and my first “first date” with a cisgender guy in around 6. When you ask me who my favorite serial killer is in your first message, you’ve got my attention as well as my heart.

Dude, it was weird. But good.

It’s strange when you’re confronted with someone new, so different from the “home” you have found yourself in for so long. Nothing is familiar.

But it’s also kind of exciting in its newness.

There’s something to be said about the nervous energy when you know the other person is contemplating kissing you for the first time, or how that kiss turns out if and when it occurs. It’s telling on a variety of levels.

This Tinder Guy and I were a really great match, but we both ended up distancing ourselves a bit towards the end of the summer to ease the fact that, the rest of the year, we lived 5 hours from each other and I was so fresh into the dating scene that I didn’t want to jump into anything.

But it was what I needed to jump-start my dating life.

When I got back into my school-year town, I decided to kick it up a notch and start using OkCupid again. That was where I met both my ex wife and my partner before her, so I knew for a fact that, with enough patience, I could have some semblance of success. Since I love stats and data, the “match percentages” calculated by your answers to my questions made weeding out the duds pretty easy.

It saved me from messaging back guys who answered the question “Do people ever owe you sex?” with a “Yes.” (UGH! Yes. People like this exist in alarming numbers.)

And it helped me find people who also prioritized education and striving for success in life. I have dated far too many people who had no drive, and it has been a thing that has always been an issue in prior relationships.

I had been looking into the idea of “Ethical Non-Monogamy” and polyamory for a while. There are lots of different ways that relationships and arrangements can look under this umbrella, but the basic idea is that someone may be seeing multiple people, always with the full disclosure that they are doing such a thing. Perhaps they have a primary partner and see secondary partners on the side. Perhaps only one partner is interested in seeing other people, or perhaps they both do, together or separately. But navigating jealousy is tricky, and, although I was interested in trying out this “lifestyle,” I wasn’t sure if it would ultimately be for me.

If anything, it was a progressive-sounding excuse to not get too close to anyone and date a lot of people to “sample” what was out there.  Which was what I was interested in at the moment.

So I started arranging dates.

I had a very selective screening process. If you simply messaged me with a “hey” or “how’s it going?” or a lewd comment about me or just a straight-up compliment with nothing else, I wasn’t interested. My profile specifically stated that I wouldn’t respond, and yet the vast majority of people can’t seem to read. Anyone I was going to date would have enough attention to detail and imagination to look at my profile and formulate an interesting introduction.

Some people were irrationally angry at my request for writing something interesting.  Exhibit A.

If someone messaged me something worth reading, I would then look at their profile and go over it to look for similar interests and red flags. If they passed these tests, I would message them back.

Even after all of this, though, sometimes they had no conversational skills and quickly lost my interest. I began to know within three or four exchanges whether or not I was feeling it. Sometimes I’d straight-up tell them that I wasn’t really vibing with them, and sometimes I’d just ghost. Yeah, I ghost. Sometimes it’s the best thing to do, because otherwise they ask why and then you have to break their heart/ego by telling them why you’re not into them. And no one wants that.  I don’t owe strangers an explanation for feeling the way I feel.

And thus began my parade of suitors. While I was open to “the right lady,” the local selection is really abysmal. Most of the women interested in dating women in my age range are divorcees with kids who are disillusioned by men and are interested in “trying women.” Definitely not the hardcore androgynous types I’m into.

And LORD, the COUPLES who wanted to recruit me into a threesome. A small sampling below:





The guy who is older than my father.  (My desired age range was listed as 26-45.  His was 50-79.  So explain this.):


The vomit-inducing:


And the WHAT THE FUCK (make sure to note the dates the messages were sent):






The strange messages from international fellas who I’m pretty sure just want a green card:




Or this guy who lives just one state over who had no idea that Delaware was a thing (is balloon balloon balloon okay sign like the new eggplant emoji or something?):


And let it be known that this guy is telling the world that I am smoking hot:




But here’s the stories of the guys who passed the screening process.  I mean, look who they had to compete with.


I actually met my first “date” on Tinder. He seemed very sweet and we had very similar personalities, but he had some pretty complicated life-stuff going on. And, while he knew from the beginning that I was going to be seeing other people, he wasn’t really that cool with it. A lot of negative elements from previous relationships began to creep in, and I realized I needed to cut it off before it progressed too much. Even though it had only been a month, there was a lot of drama while I was trying to call it quits, including nearly having to block his phone number.

Well then. This was gonna be trickier than I thought.


Along the way, I had picked up a “friends with benefits” situation, though he lived states away. We were romantically interested in each other, but acknowledged that we weren’t interested in anything long distance. But perhaps we would visit if we could engineer it some weekend. But still, some text-flirtation was fun and kept us both entertained.


I started talking with a guy from Philly, about an hour from where I lived. His job had hours that were pretty much the exact opposite of mine, but he was willing to drive out to meet me. He had gotten out of a 6 year relationship earlier this year, but had been dating for a while already. His adorable enthusiasm paired with a similar “ethical non-monogamy” lifestyle made this an ideal arrangement. It was refreshing to be able to talk with him about other partners casually, being happy for each other. But we both shared how, in the end, we missed having someone to come home to. We discussed how we didn’t know if we could settle into old age with multiple partners, but no firm foundation of a life-partner. We were still both new to this concept, and weren’t sure if it could be sustainable for forever.



I went on one date with a local bar owner who had a long-time partner but they were both poly. But for various reasons, this situation quickly became more drama-tacular than I wanted and that ended.  Like, it seriously went weird places I don’t need to go into.


There was one guy who messaged me who had a couple red flags in his profile: he had kids, he lived halfway down the state, and he stated he was interested in “settling down in a serious relationship.” He wrote me a nice message, though, so I responded and told him my reservations. He somehow convinced me to drive that night nearly an hour to meet him at a Waffle House at 11PM on a Sunday night. I, feeling adventurous, agreed to this impulsive suggestion. We had a nice enough conversation, but I wasn’t feeling any sort of spark. Everything seemed kind of forced.

The next day, I told him as much, and he both simultaneously tried to play it cool while being wholly indignant. He asked for me to give him another chance, and I told him “This whole time, you’ve been convincing me to do things. Convincing me to go on a date with someone who has several strikes against what I’m interested in. Convincing me to drive to a Waffle House super late on a ‘school night’. And now, here you are, trying to convince me that I actually liked you way more than I did. No thanks.”

A week after this conversation, he simply texted me with a “Blah hi.”

To which I did not respond.

I saw him visiting my OKCupid profile every few days, still.

A week after this, he messaged me on OKCupid, “Soooo we can’t even be friends?”

I didn’t respond.

NINETEEN DAYS LATER, he wrote “blah.”  (Seriously, dude?  You’re 30 years old.  SERIOUSLY?!)

Over a month after our single date, he wrote “Sucks that we can’t even talk, I’m not gonna try and meet up or anything to that nature.”

Ugh. So, obviously he wasn’t taking the hint that I was seriously done. I messaged him back, “Your continued contact despite the fact I rejected you has only served to confirm that I made the right decision. Please leave me alone.”

It’s been nearly a month since I sent that, and he finally appears to have gotten the message. I hope.  Dodged a bullet there.  

But, I mean…I am pretty awesome.  I see where he was coming from.



I had one date with a local grad student studying sculpture who seemed pretty cool, but he spent the whole date talking about himself and his friends and his roommates and his ex-girlfriends and girls he hoped he would have dated back home, and never really asked me much about myself. Nooooope. He wasn’t THAT interesting and not attractive enough to just look at.   After dinner, he asked me if I wanted to go with him to a bar and I delicately requested “Actually, can you just bring me home?”  I think he got the hint, because I never heard from him again.  And was glad I didn’t have to tell him he was self-absorbed and boring.


This guy looked like a total gym rat meathead.  Definitely not my type.   His profile stated he liked “fit women” and he told me that I needed to change my physical attribute descriptor from “average” to “fit.” I assured him that I was not fit, and if that was what he was into, I wasn’t it.  We messaged back and forth a bit, but all this fella would talk about is how much he wanted me to “peg” him (which is to say: strap it on and stick it in his butt) while putting him in various wrestling holds. He did not want me to abuse him in any other ways. No biting, no slapping, no scratching, no pinching. No demeaning.  You know, the fun stuff.  He wasn’t into that. But when asked what I would get in return, he was at a loss. I called him out on being completely selfish.  I told him, “It seems like what you really want is a woman who will do whatever you want her to do and you don’t care about giving her anything in return. I think you’d be better off hiring someone.”


Actually, I have gotten MANY requests for pegging.

Have you ever strapped it on and banged a guy?” is always a winning opening line.

Something about me just screams “Ass-Master” I guess. Well, Mistress.

I mean…that’s cool.



I matched with this guy on both Tinder and OKCupid. He had a similar dark sense of humor and loved watching dark and messed up stuff on Netflix like I did. He was a security guard with weird hours, but we met up one Sunday afternoon for coffee before his work shift. We had a great conversation and really clicked. We ended up hanging out again after his shift and watched the TV show Hannibal together while he bonded with my cat.  Chet is such a good judge of character.  Finally, I felt like I had met a local guy who I saw myself being able to just chill with. Even though he was older than me, he was pretty inexperienced in dating, but he was also super cool with whatever ended up happening between us.

Which, in hindsight, was very good, because…then things got even more complicated.

(I know, right?  My coworkers and classmates have often told me that they live vicariously through my ridiculous life.)



I have sent one “first message” to a guy on OKCupid, and it was to this guy.

But it wasn’t the first time I had seen him.

I first saw him last November, when I had just joined Tinder. His profile read that he was happily married, but he and his wife were looking for other weird people who broke the mold of your typical Delawareans to be friends with. Now, sometimes on Tinder this is code-speak for “threesome” but in this instance, it really didn’t seem like that was the case. He was beautiful, had shoulder-length hair dyed a deep garnet, and wore makeup.  Totally genderfuck.  Yeah, definitely not your typical person from around here. But damn, he was married. If he wasn’t, I’d totally be into him. I didn’t swipe right on him because I felt like things could just get awkward there, and I wasn’t quite sure if it was a trap or something.

But then I found his wife (I recognized her from a few of his photos, and vice-versa.) Her profile had the same story, looking for some weird queer-ish local friends. So it was legit. It seemed less weird to swipe right on her (though she was also totally hot) so I did. We matched, and at some point, she messaged me.

But at that point, I was in my deepest of depression, and never responded. Though I felt bad about it. She seemed super awesome and like someone I would like to befriend. Like we would get along super well. But I was just not in any sort of state to do anything. I was just trying to tread water.

I re-discovered her message in March (yeah, four whole months later) when I had begun to resurface back into my life and decided to write her back, apologizing for my weird avoidance and everything. But I never heard back from her. I didn’t blame her.  And, come to find out, she was in her own weird place at that point anyway.

Fast forward to August.

I found The Guy on OKCupid.

We were an 85% match, which I have learned is the “sweet spot” for people I click best with. Enough to be very compatible, but not enough that we’re carbon-copies of each other.

He mentioned cats.

He mentioned how “displays of machismo are the pinnacle of idiocy” and his distaste for gender norms and pretentious people. And Amanda Palmer/The Dresden Dolls, one of my all time favorite bands. And his love of reading Wikipedia.

And he mentioned that he had his life together until “things imploded recently.”

So…what was going on here?

No mention of a wife, no mention of an open marriage…

I didn’t know exactly what was going on, but at any rate, he seemed like the kind of guy I would like to hang out with, even as a friend. I had been craving for meeting another “weirdy” in the area. I didn’t really fit into any sort of group locally, and I had passed up a chance to connect with him once before. I wasn’t going to do it again.

So I messaged him.  I may have called him “stunningly gorgeous.”

I discovered he also worked at my university.

I discovered he was in the process of a divorce…something that had been in development since about the time I saw his and his wife’s profiles on Tinder, but only really seriously starting this summer. So new.

The more we talked, the more we realized that we had been going through some very similar things in both our marriages and our separations. That we felt very similarly about gender and gender expression, and it confused most people, but we were fine with that.

We met for coffee at Panera Bread one evening, and were both supremely awkward. I warned him of my flailing muppet arms and manic chatter when I was nervous, and I more than delivered. He was very candid with me about where he was in his life, and we felt comfortable talking about a lot of the intricacies of our lives and marriages because they were so very similar. Eerily so, actually.

The whole time, I wasn’t quite sure exactly what the motive was for all this. Was it a date? Was it a friendship audition? Was he interested in me romantically? Was he even ready for such a thing? I know I wasn’t when I was at the point he was currently.

I didn’t know, but I had a great time and wanted to see him again, no matter the intentions. I was willing to hang back and let him take the lead on where he felt comfortable with this going.

He texted me later that night, “Thanks for making my first date in years non-traumatizing.”

Awww. That was the most flattering thing I could have received. Seriously. My first date a few months earlier had been non-traumatizing too, and I was lucky to have met such an understanding guy.  And he said “date.”  So that clarified that question.

It’s so terrifying to put yourself out there again. Especially when you’re still so raw, wounds not yet healed. Only just beginning to scab over. I was honored to have been his first date in…probably eight years. Hugely honored.

This date was a few days before the aforementioned security guard guy.

And our second date was the day after.

On our second date, I realized that he was, indeed, romantically interested in me. And, in spite of the supremely complicated mess of a divorce and cat-visitation and really fresh scars he was facing, we both acknowledged that whatever was going on between us was pretty damn cool.

And this jaded, toughened, man-eating heart of mine turned to jelly.

I began to doubt my proclamations of non-monogamy, of not wanting to get serious with anyone, especially so soon. I began to feel absolutely batshit crazy.  A week before, I was enjoying the game of lining up as many dates as I could, juggling text conversations with half a dozen guys, and now, I had no interest.

At this point, I had already begun to separate the “wheat from the chaff”, as it were. To settle into a groove of the partners I thought I may “keep around.”

There was the enthusiastic non-monogamist guy from Philly.

There was my long distance friend-with-benefits.

I had one date with the Antisocial Dark Guy, but I saw potential in him.

And then there was this guy. Androgynous Guy.

I told the Antisocial Dark Guy about my situation. It sucked, because this all happened the day after I first met him in person. I told him that I had no idea exactly what was going on, but at this point it may be best if I didn’t continue to see him in a romantic sense to complicate things. He’s seriously one of the most objective people I’ve ever met, and was happy for me and was thrilled to have met me at all, and was cool with whatever came of our friendship. Whew.

I told the Long Distance Friends with Benefits guy, and he understood. We were always friends first. I decided it would be best to transition back into that.

I told the Enthusiastic Non-Monogamist Guy from Philly. He was happy to hear I met someone with whom I had such a great connection, but hoped that I wouldn’t “cut him off” completely. And I didn’t want to. Besides, Androgynous Guy and I were trying to figure out how to “take things slow” (whatever that means) so keeping Enthusiastic Guy in the mix would theoretically distract me a bit. And he was also the polar opposite of Androgynous Guy. It kept things interesting.

It’s been just about a month and a half since Things Got Complicated.

I’m gonna be honest and say that seeing Enthusiastic Guy is a little weird now. Still good, but weird. It’s just the two of them now. They both have the same first names, so that’s…handy? (Actually, The Guy I Nearly Had To Block also did too. And the Wrestling Hold Pegging Guy. For one brief shining moment, I was talking with FOUR guys who had the same first name. My life is so surreal sometimes.  And I’ve gotten messages from two more.  I’m convinced that’s one of the only male names allowed in the surrounding area.)

My ex wife is completely out of the picture. From the looks of things, I think she’s been in a serious relationship for months (maybe pushing a year?) already. But I’m extremely sensitive to Androgynous Guy’s situation, because I was right there at this time last year. It’s a delicate dance, both knowing that we’re extremely interested in each other, but allowing him the space and time to heal and figure out himself. And still trying to protect myself and take care of myself, even though I know he only has the best of intentions.

“This has got to be a trap,” we’ve joked.  “It shouldn’t be this easy to find someone who is such a great fit again.”

Ultimately, I don’t know what the future holds. At this point, I could see myself settling back into monogamy. But part of me wants to have the possibility of a primary partner with negotiation for seeing other people on a case-by-case basis. Maybe.  But I’m not sure.

Ugh, I don’t really know.

I smashed back into the dating scene with vigor, and am tiptoeing into What Else Could Be. Let’s see how this goes.


2 thoughts on “On My Adventures in Dating Again, or How I Tried Ethical Non-Monogamy And Dude, I Just Don’t Know

  1. What a rollercoaster! I’m glad you’ve been able to meet a couple of interesting people….there aren’t too many of those in DE unfortunately. But having Philly nearby helps for sure. I hope things go smoothly for you and Androgynous Guy, sounds like a complicated relationship that could totally be worth it. 😀


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s