Kat’s Adventures in Dating: The Worst Date That Turned Into the Best Date

One thing that I still have not mastered even after 25 or more years of dating is trusting my gut and saying NO, loudly, and forcefully, when I need to. I’ve agreed to dates that made me uncomfortable with men I felt iffy about. I’ve continued on dates that weren’t serving me in any way, and then just felt worse when I had to find a way to excuse myself from the event without incurring the man’s wrath or ire by informing them that they are, in fact, the worst. 

There are times when you just feel meh about a person, and that’s ok. Or you’re not ready to date and so you’re just kinda’ lukewarm, even if the person is spectacular. And a good date will ask what’s up, and you’ll be able to communicate about it, and be genuinely open to hearing your opinion and your needs, and you’ll go your separate ways, and feelings will be hurt, but you were honest and everyone is better off. 

But there are times when a guy is objectively terrible in a number of ways, and there is no way to convey this, because when a guy is objectively terrible, he is generally not open to constructive criticism. This sucks, because it means he’s just going to continue to be objectively terrible. 

Never Agree to a First Date at a Guy’s House

I will admit that my first mistake was agreeing to a first date at Gale’s house. The thing is: a “first date” at someone’s house is not a first date. It is a booty call. It should be left to booty call status. It should be done drunkenly or at midnight. If you are not sure you want to have sex with this person, do not go to their house the first time you hang. Even if they say they’re just going to make you dinner and put on some music or watch a movie. That is not what first dates at a house are for.

Gale and I had met on Bumble and he was kinda’ pushy but he had a lot of things going for him, like he was well-read, and educated, and had a good job, and he was interested in self-improvement, or so he said. (Tip: If he talks a big game about having or doing something, he probably doesn’t, like money, working a killer job, brains, or… other things. Guys who have those things don’t have to talk about them; they just have them or do them. They can show, not tell.) 

He said he liked art and nerdy things, like me, and I thought he was at least somewhat good looking from his photos. Good enough looking. I’ve definitely fallen in love with less than good looking men, right? Haven’t we all? As long as the personality is hot? 

We started with a phone call and he seemed okay enough, except he was pretty high on himself, it seemed. And he was a little too excited about how hot I was in my photos, and how great I seemed to be. (I do look good on paper, I’ll give you that. But paper is not chemistry. And if you start off thinking we’re perfect for each other before we’ve met, where do we have to go from there?) 

I was giving blood on the following Tuesday night and he said he’d make me steak and scallops for dinner at his place. So I said ok. I like free dinners. And I like being taken care of after I donate blood. And I’m a grown ass woman and I can handle myself. 

I Don’t Want to Hold Your Hand

I already had weird vibes from Gale when he asked via text if he could kiss me when I got to the front door. Props for asking for consent, yes, but he hadn’t met me in person yet. How did he know he wanted to kiss me? Why did he need to corner me so quickly? Had he already bought the ring?

When I pulled into his driveway after giving up a pint of my precious blood, I was already a little physically dizzy, and I felt even more disoriented by his dogged pursuit. I’d said no to the kiss, but he went in for a hug anyway, which, fine, okay. I’m a hugger, but I gave him the ol’ side hug, which most men would recognize as a “slow down, pal”. Gale did not appear to understand “slow down”. 

He asked if he could show me around his house. To which I of course said yes. What else were we going to do, make out fully sober on the couch? Also I was curious. He lived alone in the suburbs. What was this house? Was it a man house full of sports paraphernalia? Was it going to be a Confirmed Bachelor Pad? 

The thing was, he took my hand while showing me around his house. This was awkward. We had JUST MET and I had already declined a kiss and given him a Christian Side Hug. He was already holding hands with me, and in a very awkward way. Like, he wasn’t leading me by the hand, he was just holding my hand while walking from room to room around his house. It was weird.

I dropped his hand. He tried to pick mine up again. He hadn’t asked if he could hold my hand, or I would have said no; instead I just pulled my hand away. Which means no. I moved away from him when he got near. It was not cute. 

Who Is This Interior Designer You Hired?

Next up: his house was weird. I would have preferred Fight Club posters from college, honestly. Or a wall of signed footballs from Tom Brady that he collected.

He said he had worked with a designer and she had told him that every room in his house needed a theme. I had never heard this from a designer before, but he had liked this idea. He seemed to think it made him the most culturally learned person in the world, that he had hired a designer and come up with themes for his various rooms (which, btw, he had way too many for a single guy to have). 

I believe there was a map room – one of the guest bedrooms. It was just maps. Not of places he’d been. Possibly Middle Earth and Westeros. He had a library whose only discernible theme appeared to be “books that look old but are really just the versions that Barnes and Noble put out of classics that are in the public domain”. I doubted he’d read any of them. His media room was 80s arcade themed, I believe. There may have been dragons in the fantasy-themed guest bedroom. I do not remember what his bedroom was themed. I got out of there as quickly as I could. 

His dining room was “old art” themed. Some of it he had collected in Greece – like part of an arm from a fresco. Some of it was tacky reprints of rote art that everyone knows about but no one really likes. It felt very much like someone trying to imitate the British Museum who does not understand why the British Museum is the British Museum. 

His designer had told him to keep his full place settings out on his dining room table so that it looked homey and lived in. It looked, to me, like it was staged to be sold by a realtor from the 90s. It was not comforting. It was weird that he had place settings for eight but lived alone. It felt like he was waiting for his big ghost family to arrive and have dinner with him. 

The other thing about keeping your dishes out all the time is that they get dusty. So if you don’t have a full-time house cleaner keeping up with that shit, trust me, it looks bad. 

Men (and probably most women): your houses are dustier than you think. 

Seriously Don’t Touch Me

He kept trying to kiss me or get close to me while he cooked dinner. I kept saying I was not comfortable with it, and he kept trying anyway. Or asking. He could not accept a no. 

He offered me wine, and I declined because I had just given blood. He tried to pressure me into it, but in a really nice way. Just one glass. It would make me feel better. I emphatically said no. 

He put on opera, because we had talked about opera. It was not an exciting opera, it was probably Carmen. Everyone loves Carmen. It’s what you put on when you say you love opera but you just say that to impress people. People who know about opera exclusively because they once watched Looney Tunes know Carmen, and enjoy it just as much. 

I can’t even remember what the conversation was about because I was trying to find a way out of the house without being a big ol’ meanie bitch.

I wish I had said, “Dude, you’re making me uncomfortable. Seriously, don’t touch me.”

The truly bitchy Kat my therapist and I both wish I could be would have said, “Dude, I don’t find you attractive. Your pretentious ideals about what’s ‘classy’ bore me. I am not interested. Let me out of your dungeon.”

But I was worried in the back of my well-trained lady brain that if I said anything or made any false moves, he would maybe kill me and stuff me in his “dead woman”-themed basement. Because you never know.  

Disappointed with Dinner

Finally we sat down to eat. It was steak and scallops. He had studied cooking in Italy, he said. Because of course he had. 

It was awful. It was just plain awful. Overcooked, under seasoned, terrible stuff. Limp asparagus. Chewy scallops. And he had no idea. He was perfectly pleased with it and thought I should be, too. He offered seconds. I declined. 

I told him I was not feeling well. Which I wasn’t because I’d just given a pint of blood. And the food was bad. And he kept trying to touch me even though I clearly wasn’t interested. And I had visions of the basement where all the other perfect women were sitting lifeless but still looked alive because he’d studied taxidermy in Jackson Hole, Wyoming one summer, probably. 

He asked if I needed to lie down. I said no, thanks, I thought I’d just go home.

He kept insisting he could get me something – water? Wine? Pajamas?

No, no, thank you, I said, I just wanted to go.

From my memory I basically had to peel him off of me to get to my car. 

Verdict: He asked if he could call me. I said I’d call him if I felt up to it. And not to contact me again, basically. I think I texted him thanks for dinner but don’t contact me and then I blocked his number before he could ask why. Because there was no way that conversation was going to end well. 

The Savior Appears 

As I was getting into my car, I got a text from Senthil. 

Senthil was a guy I had also met on Bumble. We had gone out for coffee and had hung out several times. We’d gone to a rave together and stayed up until 5 in the morning dancing, totally sober. I was extremely comfortable around him. 

Senthil was hot. He was a few years older than me but he basically skateboarded all the time and was just fit and tan and cute. He was a sober vegetarian who read a lot and cared about his family. He liked to talk about philosophy (not just brag that he read about it). He was building a skatepark in his driveway for himself and his kids. 13-year-old me would also have had a huge crush on him. 

He had four kids who were all in Central America with their mother for the summer. So he had a huge house with a pool and a boat dock with a boat all to himself. 

Just Wanting to Talk (For Real Though)

“Hey, are you busy?” Senthil asked. “Just wanted to talk.”

Senthil was going through some trouble with his work. He was in the midst of splitting up from his wife, but he was also thinking about quitting his job. We talked a lot about the meaning of life and enjoying it and what was worth money and what wasn’t. So this was actually something I was interested in.

I called him and told him I was only about 10 minutes from his house on the lake. (If I’d been at my house it would’ve been a 45-minute drive.) I said I’d be right there, because I needed to get the bad taste of this date out of my mouth/hands/soul.

The Exact Right Things to Say

When I got to Senthil’s, we talked about his troubles. How he was mad at his boss, his organization, and thought he needed to quit. I validated and listened and offered advice when he asked for it.

And when we were done, he basically went through a genuine checklist of everything I think I had ever wished for in a date.

He said, “Thank you. Honestly, I had a date with a 26-year-old tonight, but I canceled it because I just wanted to talk to you.”

Music to a 40-year-old woman’s ears.

He went on, “Also you’re hotter than her. I mean she’s cute but she’s just young. I just like you better.”

Suck it, 26-year-old.

And then he asked, “Would you like a massage?”

Um, yes, of course I would like a massage from the hot skater guy with the self awareness and the really, really nice hands.

So he gave me a massage. A really good massage. Not just the massage of a guy who says he can give a good massage – a legit good massage.

And then he asked if I’d like to go stargazing on the dock.


So we went stargazing on the dock. And talked about life, the universe, and everything. And made out, because it was romantic. And he was hot. And great. And we genuinely enjoyed each other’s company. And he listened to me, and we both agreed this wasn’t going to be anything serious, and there was no pressure. 

The Cafecito

I slept over and got up early in the morning so I could get home and go to work. While I was getting dressed, he said, “Can I make you a cafecito? I have this delicious recipe.”

So I got a cafecito. And it was, in fact, delicious. 

Then he let me leave of my own accord, in my own time, and I drove home in the pre-dawn listening to love songs because I felt pretty damn great.

Verdict: Senthil and I hung out a bit more over the summer going on dream dates (An evening on the boat on the lake! Dancing! Helping me write erotic stories! Bubble baths!) but we eventually drifted apart. We still follow each other casually on Instagram, I think. He may have gotten back together with his wife. But I still think fondly of how he told me I was hotter than a 26-year-old.

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