#18 THE DATE WITH THE GUY WHO WORKS FOR A HUGE TECH COMPANY, A MAN WHOM I’LL FOREVER ADORE
Some people radiate kindness and give you the warm fuzzies, even when it never quite works out
To get the context for the title story, this is really the story of three people.
Person 1: Ethan
In Middle School, I met this guy – we’ll call him Ethan. I met him again when I was in university. Ethan lived in another party house but on the other side of campus, the opposite side of my side of town, but not a million miles away. Through him, I met someone we will call Clay. I’m not sure how I ended up partying with these boys but I was still dating my High School Sweetheart (HSS) and he came along too.
Unlike the International Boys, these guys had Jello Shots and a surprisingly well-decorated house for a bunch of college guys who mostly played Call of Duty or some such during the day when not in class, shouting at children over their headsets. All the boys had been rich types who hailed from Tifton (where I’d gone to Middle School) and I had known them once or knew of them. Family lineage and reputation are big factors in the South. One of their parents had bought the house as an investment for them all to live in but in the bathroom during parties, they had a giant stolen gas station toilet roll wheel tied to the toilet roll holder with twine. It’s the little thing we often recall!
Ethan seemed cool and sexy because sometimes he’d take me on the back of his motorcycle where he wore all leather, which seemed oh-so-appealing. He was handsome and very sweet to me. I remember the thrill of holding onto him, pressed as close as I could get, legs straddled behind his, as we whizzed around town. Once, before I went to England for the summer (probably 2008ish), I kissed him. I wrote about it in one of my diaries (I was a very infrequent diarist) and I was still with HSS. How did I keep up with all of my crushes and connections? SMH!
I don’t remember all the timelines but this kiss was the seventh person I kissed (thanks to my actual list I kept back then – and HSS was only the fifth person I’d kissed) right after the second person I’d slept with so I was still naive and inexperienced and a little delicate.
I wasn’t in a rush to sleep with Ethan. Once or twice, I’d slept over at his house in his roommate's super king-sized bed, not sure why I didn’t just go home. The roommate was never home because he slept at his girlfriend’s place every night and even though he locked his room the guys in the house knew how to unlock it to let people sleep in his room (poor guy, also pretty gross for him).
I think one night HSS had slept over too – I guess Ethan’s game was to be nice to me and my boyfriend in order to get me? Odd! I remember one morning I looked into his room because the door was open to find that he’d drunkenly pissed the bed and was sleeping in a giant wet patch.
Later, after HSS and I had broken up, I tried to make something with Ethan but I was too nervous to sleep with him so never did. HSS had called him (in the days when we all still had flip phones) to ensure Ethan knew that I was still sleeping with HSS from time to time, which Ethan didn’t take too kindly.
Ethan, in creative spirit, took the time to spray paint “GET OUT” on the side of a discarded piece of chipboard or plywood in the carport. I think I’d slept over at his house, curled up in his single bed with him. When I came outside to see him on the phone, getting the sense he was on to HSS, I had that sinking in the pit of the stomach feeling. Ethan had tears of anger in his eyes, quietly seething. He was a kind, quiet kind of soul. I saw the spray-painted sign; he was quietly looking over at it, and he didn’t say a word. I left. I didn’t try to explain.
I gained my freedom from HSS mostly when I’d moved into my Slater Street house and I think Ethan had borrowed his friend’s pickup truck to help me move stuff into my new house so he definitely deserved better.
He unfriended me on Facebook and moved on with his life, presumably. There’s no internet trace of him now so I hope he’s had a good life since. He was a tall, handsome, blonde-haired-blue-eyed sweet man so I’m sure he is just fine.
And, really, what I did (i.e. not sleeping with him and still on and off hooking up with my ex) was not about him at all. It was entirely about the fact that I’d only had two sexual partners and one of them had flat-out said after sex I meant nothing (and this was before I’d slept with the hot married professor). Life was a cruel teacher. I didn’t want a repeat of that scenario.
Person 2: Clay
Now to Clay. Clay had Southern charm and charisma. He was very handsome but on the shorter side. A frat boy with character. Once, he showed me a picture of his tall, handsome “wingman” (we’ll call him Theo). He sang Theo’s praises like he was the coolest guy on the planet and they’d hit the bars together hitting on girls. I was intrigued.
Since Clay was the twenty-eight person I kissed, I re-met Clay long after the whole Ethan debacle and after I’d slept with ATC. But I’d met him originally around those Ethan times at one of those parties on the other side of town.
Before I actually got to meet Theo, Clay and I would have odd encounters where he’d come over to my house, we’d sort of get each other off with our hands, he’d oddly dry hump me, we’d make out, and then we’d chat into the night and fall asleep – and off he’d disappear for days, weeks, months. We never actually had sex; he never tried. Even then I looked on these encounters as puzzling yet funny but I wasn’t too invested. I remember him talking about alien conspiracy theories and all sorts of what seemed very “interesting” ideas at the time.
He seemed like this clean-cut trust fund guy and here he was having non-mainstream ideas. As I said, he never tried to have actual sex with me. I later had a few other flings where we had this sort of thing where it was a case of mutual masturbation and that was that. Maybe I was that person who helped stave off the loneliness and existentialism. I heard a rumour that Clay had his heart badly broken by the girl he wanted to marry but I don’t think we talked much about that.
We are no longer FB friends but it looks like he works for Rutgers, is married, and has a child now. In true Clay style, a few of his FB photos are of him in a tux.
Somehow through Clay, I eventually met the charming Theodore or Theo for short. Theo was a tall, gorgeous man, whose laugh would crinkle the corners of his mouth. He lived in another party house when I was in grad school, on the edge of campus, where I met another of my hookups years later (where I went full-on hot-crazy scale-level obsessed) but that’s a story for another day.
Person 3: Theo
So, in December 2009, somehow I ended up on a date with Theo at a friend Randall’s birthday party.
I met Randall and Andrea who both worked with me at the tutoring centre, the SSC, where DJ had also worked (i.e. the second person I slept with who had cut me down). Andrea was a literature major and English tutor like me and Randall tutored science, physics, and mathematics.
I adored Andrea and Randall. They’d dated since they were young. They were high school sweethearts (who are still together where he’s an engineer and she’s a debutante businesswoman) and they own a cattle homestead/ranch where she attends charity galas and throws glam parties and looks like the gorgeous blonde version of Audrey Hepburn but with the Hollywood smile – and the perfect looking children.
They were (and are) a beautiful, magnetic couple, and full of kindness in the way that naturally happy people can be kind. Things in their world are magical for them, things work out, and they spread their kindness like fairy dust.
Theo was the same sort of person, the kindness and warmth radiated from him. He grew up in California so he had the cool Cali vibes that every single person I’ve met from California seems to have. His mother had attended Sarah Lawrence and I can’t remember what his father did but they were still happily married – a happy loving, secure family.
He was a computer science major (which would pay off in his future big time via his hard work too of course), who took some advanced mathematics courses with Randall, which is how they knew each other. Theo was kind, charming, and handsome – and he somehow asked me along to this party which I think I’d already been invited to anyway.
We were sitting on the sofa where I was happily curled into him holding his hand. I loved his big, tall, strong body. His hand felt secure in mine. I felt at peace after the drama that had been my breakup with HSS, the string of all the next people I’d dated who were equally wrong for me, and the men I’d had flings with, and there was this lovely man holding my hand with his caramel skin, brown eyes, lovely textured hair, big smile, kind demeanour.
In walks HSS. He had evidently also been invited.
Theo, being a nice human, spots HSS not knowing we had a past and is like, “Oh, hey, man! You’re in my [whatever mathematics class].”
HSS looks at him, sees us holding hands, and pointedly and sharply says as he stabs a finger in the air towards me, “That’s my ex-girlfriend” and walks out to the balcony to take up his new hobby of smoking. I wanted to die.
Turns out HSS had, like everyone who ever met Theo, thought Theo was, very rightly, a super awesome, cool human because he unequivocally is one of the best men I’ve ever met (right up there with my own precious Michael).
We made out that night, he slept over, barely fitting on my bed. But we didn’t sleep together because Theo’s “down there” proportions were more than I wanted to handle given my then-limited experience. I probably gave him a handjob but I don’t remember. I guess what did I expect from a man who was taller than 6’4” with a huge, solid, muscular build?
But I did sleep with him a year later after I untangled myself from the disaster that was the Stella Adler Actor. I’d gone over to some form of cold December Christmastime pyjama party at Theo’s house (on the 12th of December according to my FB photo album). Theo always threw epic, themed parties.
Four of the guys who lived there were university students but one, interestingly, worked as a cameraman for ESPN sports, a job he loved, and he had a dog but because his job required a lot of travelling he liked living in this house full of guys who would look after his dog when he was away. He also didn’t mind the parties when he was home.
They used to use their kitchen door as a bar area. They’d create a makeshift hatch which maybe was wood nailed up between the door to bar entry, and you could go to the “bartenders” to get your drinks, glow sticks, and nitrous oxide.
The boys always had beer pong set up in the dining room and people would congregate in various areas of the house – the dining room, one of the two sitting rooms, near the kitchen door – including the big front porch. They’d have loud music, cool people, sometimes a fog machine, always a vibe.
I’d gone to the party with Darcy feeling despondent at my latest breakup. I think she’d gone with her latest online date, usually military guys (before I had my own military guy streak). It was cold so I wore pyjamas (nightclothes being the party theme), a dressing gown, and a woollier coat on top. My hair was in braided pigtails. Other girls took the theme as if it was a Halloween extension and were wearing sexy slips or lingerie. I was not looking cute. I was dressed to cocoon myself from heartache. I met another guy there that night on the sofa and exchanged numbers but I’ll tell the story of him later.
After the party had died down, I slept in Theo’s bed and decided that I’d brave his massive, scary cock. I remember a lot of smiling and laughing and spooning after we’d showered. The next morning, he took me to breakfast but I was still wearing my pyjamas so that was the most awkward breakfast ever, yet, as usual, I enjoyed his company and he seemed not a bit embarrassed at going out with me dressed like a cosy bowling ball.
We’d hook up from time to time after that but it was harder for me to make him come because he couldn’t go hard, fast, or deep with me without it feeling like birthing a cucumber or having to poop in the wrong big. I was definitely all about big penises but I had a limit (between 7 and 9 inches only, a decent amount of girth but not enough to make me walk like a cowboy).
The sex was always good – comforting in a way – because he was someone I absolutely loved to death on account of him being the nicest human ever. He thought I was too vanilla, too innocent. He liked his sex a little on the kinkier, dirty, more adventurous side, but felt I was too innocent to be party to his deepest fantasies. I’m not sure why he had this impression of me that I was super innocent. I guess I hid my semi-promiscuous activity well even though I seem to have kissed half of Valdosta. And I’m not sure why he thought I was so innocent when years later he told me he had thought I’d been hooking up with Clay – not sure where or why he got that impression, though, because Theo was probably the only person besides Clay himself that ever knew he came round to my house the odd time or dozen.
I asked Theo for examples once of what kind of stuff he was into but didn’t want to sully me with those thoughts and he had merely said that he let a girl play out her fantasy once, peeing on him in a bathtub, never divulging what it was he was missing with me.
I think we both felt that way about the sex. We adored each other but that raw, hot, amazing spark you want with a lover wasn’t there, which is maybe a shame. But maybe not as I later found that with Michael and he found that with his absolutely stunning (and uber-successful) wife.
We had hot moments, though, like the time I invited him over for Key Lime Pie (as a ruse) because my air conditioner had broken and I wanted company. Why I hadn’t just asked to bring the pie to his house where we could have slept in lovely cold blasts is a mystery.
We had amazing shower sex where I practically climbed the side of the shower to reach him since he was so tall, holding on for life, in a good, hot way. He pressed me against the tiny corner shower where his tall, big frame plus me barely fit. I always did love good shower sex!
We remained close friends. I never thought he was that into me as I’d heard rumours he had a crush on someone else, but I’d go to his parties, he was one of my fave people to have lunch with and hang out with, and we are still in touch today.
He’d invite me to go swimming with him, play on his ultimate frisbee team (I was shit), and play on his intramural softball team at uni (I was also shit at that). Running had been my only “sport” and I’d long given that up in favour of party hopping, beer pong (without drinking the beer), flip cup, and recreational sex.
There were two such lovely California men in my life (at different times) who I’d hooked up with and thought were the most amazing kind humans, but either they hadn’t wanted a relationship with me, or I hadn’t (or I’d been too trauma conditioned only to like men I had to chase) or somewhere in the middle; this kind of arrangement worked for us. I’ll write about the other one (also a Californian as mentioned) who is now a hotshot CFO/finance director another time.
Theo, his friend (not Clay a different guy we will call Mick, who I’d briefly kissed a few times and had a flirtation with because of Theo’s parties), my ex Stella Adler Actor (a pity invite because I didn’t want him to spend Thanksgiving alone), Brittany, Darcy, a few others, and I all had a Friendsgiving (Thanksgiving) meal together one year. Theo asked me to make the sides and he brought the giant, delicious turkey. It was a fun night.
When my ex-husband decided to end our marriage abruptly and I was living in icy Minnesota, Theo was attending a wedding of our other friend in Wisconsin. I hadn’t been invited because there were lots of FB photos of me cuddled up to the friend, me on his lap or our faces pressed together, (he was also one of the truly nice humans who later dated a housemate of mine) and even though we’d never had sex and only made out a few times, I guess I was not the kind of guest the future wife wanted.
I did meet her for a night of drinking in their room before the wedding but she was icy with me even though I tried to be unassuming, nonthreatening, and friendly. I suppose you can’t make everyone like you! The old friend did invite me to attend the wedding but I didn't want to wedding crash or piss off the bride.
But Theo invited me to hang out in his wedding-duty off-times on the weekend. I had to drive something like five hours to get there in my little Audi convertible that had driven me from Florida to Minnesota not long before.
It was a comforting time to me when we caught up, hung out in the hot tub in his room, and spooned as we slept. We didn’t have sex again as I was technically still married (and felt tender, heartbroken, and confused) and he had a lovely girlfriend (a different girl than the one he married) back in New York where he was living at the time but having this old, lovely friend was a solace.
Now, he is a wealthy man, high up in one of the largest, most recognisable tech companies in the world, but that would be telling. He does things like TEDx talks and runs free courses via the tech giant and I’m so incredibly proud of all he has achieved. He has a stunning, equally successful wife, a cute ginger cat (he’s always been an animal lover), two sons, and they live happily together in California in an actual beautiful house they can afford (unlike most Californians).
I follow his success on LinkedIn as he’s long since deactivated his FB (probably because of the streams of embarrassing uni-days photos) and we text from time to time to check in. He’s still the loveliest human and loves all the stories I tell him about Michael and how lucky I feel I am to have found him. I love the videos I get of his son playing in the park – and the odd picture of his newborn.
Next up, the guy who I found addictive, the red-haired sex god (RHSG) – we will call Bramwell.
Don’t forget to check out the other seventeen posts I’ve written, including the one on why I’m writing this newsletter/blog in the first place.
If you want to share in the comments, have you ever found friendships with former hookups or do you think these friendships aren’t possible? Let me know.
