Archives for category: Older Men

My dear readers know that I’ve been on a lot of dates. And a lot of really bad dates. But this was, perhaps, the worst date I’ve ever been on. Not because he was mean or anything, but because, from the second I said hi, I wanted to leave.

Instead, I stayed. For two hours.

Let’s back up, here.

This guy messaged me on OKCupid. He was very tall (yes), bearded (yes), and kind of chunky (yes), so obviously I replied.

There were some red flags. He was 49, and I’ve learned that, at that age, there’s usually a reason men are still single. He had never been married, which was good, for me, but also – had to be a reason. But he had no kids, and he owned a brownstone, so he was basically landed gentry in Brooklyn. If we fell in love and got married, I’d basically be a marchioness.

Also, he had three pictures up online. In two of them, he looked attractive, chunky, bearded, normal. In the third he looked really, really awkward, leaning slouchily against a bridge in a pair of sweatpants and an ill-fitting t-shirt. But the other two looked fine, and we were hitting it off so well, that I ignored that flag, too.

We had amazing nonsense banter. I love to be silly and talk about nothing, and we talked about such silly nothingness. Over text, I thought he seemed smart and interesting and down with a kind of bossy woman, so I was really looking forward to our date.

Almost immediately, we connected on how we both liked black licorice. That’s a special connection to share, because not many people understand the nuanced beauty that is a black licorice wheel. It’s one of my favorite things. Licorice is even made with wheat flour, and I love it so much that I pretend it isn’t. And it never makes me sick. Licorice is so magical, that, unlike anything else with flour in it, it doesn’t make me vomit. One bite of crusty bread? Vom-town. Pizza? Puke city. But, out of the power of love and sheer force of will, licorice doesn’t make me sick. I flat out refuse to be allergic to licorice.

But I digress.

I mentioned how hard it was to find good licorice anywhere, and he told me about Economy Candy, an old-fashioned candy store on the Lower East Side. And, of course. If anyone was gonna sell black licorice and cheap candy, obviously it was gonna be a store on the Lower East Side. He suggested we go there on our date, and I immediately agreed.

I was thrilled. What makes for a better first date than a trip to a candy store? Answer: nothing, except for an evening of champagne and oysters, because that trumps everything. He suggested we get breakfast first, in my neighborhood. Lovely. And, because we were going to the LES, I looked up my favorite pickle place, The Pickle Guys, on Grand Street (side note: I discovered The Pickle Guys because they were next door to the Judaica shop where I bought my tallis for my bat mitzvah. That’s how good these pickles are. I’ve remembered and drooled over them since I was twelve). A plan was in place that I felt good about. Breakfast. Then candy. Then good, old-fashioned, kosher full-sours.

I woke up the morning of our date bright and eager to meet the guy I had been texting with. He seemed so smart. So interesting. So, at 9:00, when I realized I wasn’t falling back asleep, I suggested we meet up earlier than planned. He agreed, and we set a revised brunch time of 10:30.

The diner is only a few blocks away from me, but they’re long blocks, and it was chilly and drizzling. I was cranky, but still hopeful. I had a good podcast to listen to. I was meeting a tall, chunky, bearded man. I approached the diner, feeling good.

And then I saw him. And I knew this date was not going to go well.

The guy was wearing a too-tight, pallid yellow polo shirt, and olive green cargo pants made out of windbreaker material. They were also too tight, and about two or three inches too short. What I thought had been lumberjack-scruffy in his profile pictures was really just unkempt.

I had made a mistake I’ve made before: mistaking super awkward and maybe a little autistic for smart and quirky. There’s a thin line that divides the two. It can be hard to determine which side someone stands on, through text and the internet. But it was clear that, this time, I had judged wrong.

I walked up to him with a smile on my face, already dreading what was to come. He went in for a hug, which I hate from even the most attractive, charming stranger. Don’t touch me. You don’t know me. From this gross guy, it was even less palatable.

We walked into the diner and the host led me toward a booth.

“Um,” the guy said to the host, with a really fucking irritating smirk on his face. “Come on!”

The host smiled and redirected us to what I soon learned was the guy’s usual booth. Turned out my guy was a “regular” at the diner. And he basked in the imagined glory of that status. He was performatively chummy with the waitstaff, and made a big show of them already knowing his order, and knowing what table he sat at, blah blah fucking ugh.

“They might bring some weird stuff over for us,” he said, smiling a weird, playful, irritating smile.

Sure enough, the waiter brought him a few assorted things – seltzer water with cranberry juice and a lime, and a plate of wheat toast with honey and cinnamon? Each time, he looked at me smugly, as if expecting me to be impressed.

The waiter came back to take our orders. The guy was still kvelling (I wish I could show you how obnoxious that smile was) and said, “the usual,” followed by some apparently special insider code words to clarify his order. The waiter then turned to me, looked back at him, said “She’s so pretty!” and then took my order. I wanted to die. Literal death seemed better than the prospect of sitting through a meal with this man.

I’ve developed a rule that I don’t laugh or smile if I’m not truly amused by something a man says. Just because I’m out with someone doesn’t mean I need play stupid girl and smile and laugh at anything a guy says. Especially if it’s not funny, or just fucking irritating. So I sat through our entire meal barely talking, miserable, trying not to flip the fuck out and be mean to this sad, irritating, awkward man.

After what felt like an eternity, I had picked at my scrambled eggs, he had eaten his broccoli-cheddar omelette and short stack of blueberry-ricotta pancakes (I heard all about them, apparently they were called “Danish” style). He paid. We left.

But the date wasn’t even close to over. We walked to the subway, and I tried to make awkward small talk. Then we got on the subway. I sat next to a man wearing horrible cologne, so I had to get up and move to the other end of the car. That provided a little bit of conversation. For the entire trip, I sat with my arms crossed across my chest, as closed off as possible. When we got to our stop and stepped outside, it was raining.

I am a baby about bad weather. I hate being cold. I hate being wet. And it was wet, and cold. I had to go into a drugstore and buy a $13 shitty umbrella. Then we had to walk ten blocks, in the cold, nasty rain, to the candy store. In near-silence.

And then, one, bright, shining moment, in a cold, rainy, dark, dark day.

Economy Candy.

It. Was. Amazing. A magical Mecca of candy, packed into a little crowded storefront. The owners were not Jewish, as I had expected them to be, but the candy exceeded expectations. I bought four pounds of black licorice wheels, a quarter-pound of Dutch salted licorice, a half-pound of chocolate-covered apricots, a half-pound of mixed loose candies (Mary Janes, Tootsie Rolls, Bit-o-Honey), and a pound of red licorice shoelaces. All in all, I blew $30 on candy. I do not regret it. It was beautiful and inspiring and an experience that I will not forget, for the opposite reason of why the rest of the date is something I will never forget.

We left the store. I knew I couldn’t sustain any more time with him, so I told the guy that I had promised to call my friend after we left the candy store.

“How’s the date going?” my friend asked, when he answered the phone.

“Not well,” I said.

“You ok?”

“No,” I said. “Can I come over?”

He laughed and said yes. I told the guy that I had to go meet my friend. He insisted on walking me to the subway.

I was still basking in the glow of all the black licorice I had just bought. I actually considered going to get pickles. No, I didn’t want one more second of this man’s company, but – I mean, those are some damn good pickles. Ultimately, I decided against it and cut my losses. When we got to the subway, he gave me a hug. I returned the saddest, most anemic hug ever, and pretty much ran away. Over my shoulder, I heard him say, “I hope the debrief with your friend goes well!”

I was free. I ran down the subway stairs in my rainboots in a state of shock and relief.

Ultimately, the day ended well. I met my friend and got out of the rain into a cafe. I had a Perrier with lemon. Then some very good bone broth. My friend and I sat in a park and watched pigeons for an hour. I met a very short old lady who told me all about her labradoodles, Bert and Ernie. Ernie jumped on me and got mud all over my sweater, but he also gave me some kisses, so that was ok. Around 4:30, I headed back to Brooklyn, with six pounds of candy in my tote bag. The day had been salvaged.

But I really cannot recall a worse date, ever, in all my history of bad dates. It was just so painful. So excruciating. It felt kind of like when I did a sleep study and had to try to sleep with a tube up my nose and electrodes on my head. I was so uncomfortable, but I knew that I couldn’t leave. Up until today, that was the most trapped I had ever felt. This date was, at the very least, a close second.


Earlier today, I got a text from a guy – what I thought was a picture of a white goose.


I looked up the area code, and it was Northern Virginia. I assumed an old flame from DC had found my number and contacted me, which was great/creepy as hell.

Anyway, as you can see, he had tried to send me a swan. An ugly duckling who turned into a swan, that is.

But here’s the thing, I was sure. Swans don’t look like that.


That picture was def not a swan. It was a goose.

This is a swan.


That? Not a swan.

Nice try, dude. As my dad would say, “Close, but no cigar” (anyone know where that phrase comes from? I have no idea).

Later, I found out who it was. Some guy who had given me 50 bucks and waited for a locksmith with me one time at an Exxon in Virginia five years ago, when I locked my keys in my car. So, that wasn’t weird at all, or anything.

Anyway, further research showed me it was a trumpeter swan, which looks different from the mute swan (the kind with the orange face). I was wrong, he was right.

But it was still creepy.

I recently changed my Tinder age range to be ages 28-49. I know. I’m 27. That’s absurd. But we all know I have a major thing for older men, so I thought I’d indulge it.

So when I got a message from a guy who was 46 (yes, that’s 19 years older than me, and 11 years younger than my parents, but who’s counting?), I responded.

My Tinder profile says, “I’ll never turn down an oyster.” Which is true. I love oysters. This guy messaged me saying, “Now you have me wanting oysters. When can we get some?”

If you want to buy me oysters, I am always on board. Plus he was pretty cute. Plus he had a beard. And it was gray. So I was in the bag.

We talked for a while. He seemed into the sassy Jewish American Princess type (aka, my brand). It was going well. But then I ran into an issue.

The number one problem with older men is that they often come along with kids. This guy was no exception.

“You don’t have kids, do you?” I asked.

“I do,” he responded. “One. He’s ten. He’s great. Is that a problem?”

It was a problem. But I didn’t say so. After all, it would be kind of fun to be the obscenely young step-mom that no one wants to mention at Thanksgiving. I could try to get the kid to call me “mom,” and then, one day, his father and I would have our own kids, and he’d feel alienated and like his dad had replaced him for a new, younger family. That sounds pretty fun. So maybe I do want to take on a ten-year-old.

Anyway, the Dad suggested we get oysters at Grand Central Oyster Bar (yes, please) and make use of his Yankees season tickets. That sounded like a major time commitment for a first date, but both of those activities were so tempting. I agreed.

And then I had second thoughts.

“How about we do something more casual first?” I suggested. The game wasn’t until Monday, and it was Friday. “I usually take the dog on a walk through the park on Saturdays. How about you join us?”

“Can I bring my camera?” he asked.

I forgot to mention that he was a photographer. Well, a lawyer who primarily identified as a photographer, which is one of my pet peeves – no, you’re not a photographer. You’re a lawyer. Own it. But he had sold photos, and did have a show coming up, which really made him as legitimate a photographer as I am a writer.

I told him he could bring his camera. We made plans to meet at 1 pm the next day.

“This sounds fun,” he said. “I’ll see you then.”

We met up, and he was perfectly good-looking. He was tall, which was a nice surprise – the men of online dating are usually really short. But then he talked, and he had a really annoying voice. I immediately had doubts about our future together.

We walked, we talked. I brought up the full-sour pickles I had been experimenting with for weeks, he mentioned that he really liked pickling okra. It was fine. Whatever. We went into the park. It was a nice day in the shade, although really, really hot in the sun.

Here’s the thing about taking a walk with the dog as a first date. There is literally nothing to do other than talk. Like, not even the quick respite that comes with sipping on your drink, or taking a bite of food, or going to the bathroom. It’s just all talk, all the time.

And he was the worst when he talked.

“I hate when parents reprimand their children in public,” he said.

“Really?” I replied. “So, like, what do you do when your child is kicking an elderly woman on the subway?”

Great, I thought. Another one of those awful parents who doesn’t say no to their child. Or take them out of restaurants when they’re screaming. Lovely. Ten points for this guy.

He insisted on showing me his photographs. Like, over and over and over. And sure, they were fine. A sunrise over the Brooklyn Bridge. Some artsy silhouettes of people walking through a tunnel in Central Park.

Throughout our walk (which was a long, long walk, as I got lost in the park), he kept making really, really not-funny jokes. Soon, I wasn’t even trying to laugh, or smile. I just pretended I hadn’t heard him. Because I didn’t know how to respond to his erudite commentary on people who dipped their fries into ketchup instead of putting the ketchup all over them, or people who ate M&Ms one by one instead of by the handful. It was excruciating.

“I like that we can just be here, and be quiet, and not have to talk,” he said, at one point. We had been walking and I had been ignoring him for a while, by then.

“Yeah,” I said. “I like silence.”

I was starving, and getting cranky. Or, as he said several times, “hangry.” Which wasn’t cute or funny the first time he said it. Don’t worry, though. He repeated it at least twice.

So we dropped the dog off at home and went to get food.

Why, you might ask, didn’t I just ditch him and go home by myself?

Fair question. I guess I was hoping to get a free meal out of it. I mean, the date had been so bad, didn’t I deserve some recompense?

As we were walking to get food, it started raining. Not just raining. Monsooning. It was a serious July-in-New-York thunderstorm, and those don’t mess around. By the time we got to the taco place (the closest food I could think of), I was soaked and very, very cranky. I do not like being wet. I do not like being uncomfortable.

I mentioned that to him. He said, “What? I would never have guessed,” with a clever little smile, as if he knew me inside and out and understood all my little quirks. It was annoying. I ignored it.

The only seats were outside – so rain kept blowing under the awning onto me. It took forever for my food to come. And I was already with an incredibly annoying man. I was not happy. Not. Happy. I didn’t even want to drink, and that’s a major, major red flag, for me.

While we were waiting for our food, he told me several times how much he had enjoyed himself that day, how much he liked me, blah blah. He showed me a few more photographs. I tried to smile. It was difficult.

Finally, after we’d eaten, I extricated myself. I gave him a quick awkward hug good-bye. Then I ran to buy cigarettes and go home to my dog, who never, ever says annoying things.

I sent the guy a nice text message:

“Hey,” I said. “It was nice to meet you, but I think I’m gonna cancel on Monday. I wish you the best.”

A minute later, he responded.

“Yeah, it was cool meeting you and the dog, but I didn’t really feel anything.”

Cute defensive text, dude. Especially after you had just spent half an hour telling me how great of a time you’d just had and how much you liked me.

But whatever. If defensive gets him off, that’s fine with me. As long as I didn’t have to sit through oysters and nine (or ten, or twelve, or fourteen) innings of a baseball game with that annoying ass motherfucker. Be well, dude. Be well.

I’m still kind of sad I won’t get to be the shitty stepmom to ruin his ten-year-old’s life, though. But I’m sure another lucky woman will fill the role almost as well.


I’ve been trying, for a while now, to find some serious scum.

I feel like the blog has been suffering – I’ve just been on too many dates lately with perfectly pleasant, decent men. So I decided it was time for someone awful.

I found the musician on Tinder. His profile was basically just references to his band and links to his music. The more I dug in, I found out that he played guitar – and guitarists are always the worst. I didn’t even think he was that cute. I was sure that I had found my scum.

“I hope he mansplains music to me,” I told my friend.

We came up with some leading questions for me to ask; questions that could only be answered in an obnoxious way.

On the night we were supposed to go on our first date, he texted me to reschedule. He had to work late, he said, could we do tomorrow? I agreed. Then, the next day, he told me that he was running late. An hour and a half later, we finally met up.

“This bodes well for an awful date,” I texted my friend. “He’s already an hour and a half late.”

When I got to the bar, he was standing outside. As I walked up, he turned out to be good looking, with a sweet, gentle face. He smiled and apologized for being late. We walked into the bar, he bought me a drink, and we sat down.

Immediately, he started asking me about myself, entirely earnestly. He asked me about what I liked to read, wanted to hear why I loved cults, and clearly just liked listening to me. I even tried to turn the conversation around; to allow him to be an asshole.

“So, you’re in a band,” I asked.

“Yes,” he said.

“Who were your influences?”

That was one of my planned questions intended to trap him into being pretentious. Instead, he turned the conversation right back to me.

“I mean, who doesn’t cite Jimi Hendrix?” he said. “Have you ever seen him play live?”

The musician looked me earnestly in the eye, waiting to hear what I had to say about the man he said had shaped his understanding of music.

The whole night, he just asked me questions – about books, about politics, about my life. All he wanted was to listen to me talk. He was enthralled. Which is something I experience, from time to time – men wanting to hear a smart girl talk about things.

So, he was a disappointment. Not an asshole at all. Just a nice guy who wanted to hear my thoughts on life.

When I was 17, I spent the summer in Brittany, France. I was working as an au pair for a family friend with a home there. Every week, I took care of their kids, but I spent my weekends in Paris.

Each time, I stayed in the 6th arrondissement, on the Left Bank, in the tiniest possible room at the Hotel Bonaparte. Right around the corner was my favorite parfumier, Annick Goutal. And a short walk away was the Jardin du Luxembourg.

I spent my first weekend there wandering down tiny alleys, going into quirky shops, drinking espresso and eating incredible croissants. I visited the Musée d’Orsay, in a fabulous old train station. It was incredible, and, by the time I got home each night, my feet were in excruciating pain from traversing the cobblestone sidewalks.

On my next trip, I went for a stroll in the Luxembourg Gardens. They were gorgeous – acres and acres (I don’t actually know how big an acre is, but I’m just gonna go with it) of perfectly cultivated flowers, trees, and paths. Soon, it started to rain – the kind of summer rain that soaks you through and through. It wasn’t cold, but it was very, very wet, so I sought shelter under a gazebo with dozens of other wanderers.

Under the gazebo, I struck up a conversation with an older man. He thought I was French, at first, because I “didn’t look like an American,” I was “too natural.” Of course, I was flattered. He didn’t speak any English. But I spoke fairly fluent French, which I was eager to practice.

We talked about politics. I explained the American electoral system to him, in French, which I thought was pretty impressive – the electoral college is hard to explain, even in English.

He told me he was 34 years old. I told him I was 19, which seemed extremely old at the time. Much older than 17. I told him I was in college, studying history. I lived in my own small apartment in New York.

I had just broken up with my high school boyfriend – he was my first love, and I was absolutely devastated. The attention from this older Parisian man was exceptionally flattering, and I melted under its influence. I so needed a man to tell me I was charming and beautiful, and it didn’t hurt that we had met sheltering from the rain under a gazebo in an extremely romantic, beautiful, sprawling French garden.

When it stopped raining, the man and I started wandering around Paris. I wanted him to take me to fabulous local places, but he didn’t really get the memo. Instead of taking me to quirky restaurants and shops on Rue Saint-Michel, we took the tourist route and went places I probably wouldn’t even have wanted to visit on my own. We went to Sacré-Cœur, a gorgeous church in Montmartre. It was pretty gorgeous, sure, but I wanted cool Paris culture! We went to the opera house and made out on the second floor balcony.

I should mention here that I, frankly, wasn’t attracted to him. In fact, he kind of grossed me out. But I was very, very attracted to the idea of a Paris romance. And he was exceptionally romantic.

So we made out all over Paris. He called me “cheveux d’or,” meaning “golden haired.” When he tried to describe the meaning of the word “chevalier,” I misunderstood “knight,” as “cowboy.” He teased me about that all weekend.

When the weekend was over, I got on a train back to Brittany. He accompanied me to the train station, telling me poetically how much he wanted me to stay, how he wished I didn’t have to go. He told me that he’d email me all week, and couldn’t wait to see me the next weekend.

Over the next week, I got daily emails from my Paris boyfriend. He called me his golden-haired princess, and signed his emails, “your cowboy.” He wrote me poetry. Yes, French men actually write women poetry. Like, entirely un-ironically. Even at 17, I thought it was total bullshit, but it was still kinda fun.

The next weekend, my last in France, I went to Paris again. Once again, I spent the weekend with my Paris man. As the weekend went on, I was more and more repulsed by him, but the whirlwind Paris romance was just so, so appealing. I don’t really like 19th century novels, but I do love the tropes – and nothing says “19th century novel” like a Frenchman writing you poetry and making out all over Paris.

Our final night together, he took me to dinner. He told me he wanted to get lobster – a huge, huge luxury in Paris, where they were probably imported from Maine. I didn’t mention that I could get plenty of lobster for, like, 25 bucks anywhere in DC, and hadn’t come to France to eat lobster – but it was still sweet that he was trying to treat me to something special.

So we ate our lobster meal. After dinner, we went into a photo booth and took a strip of three very happy pictures.

Finally, I told him I was tired, so he walked me back to my hotel. On the street outside, he took me in his arms and kissed me. He had tears in his eyes, and told me, for the thousandth time, how much he wished I lived in Paris. I nodded, by then desperate to get away from his grasp. The fact that he was kind of gross and smelly finally outweighed the romance of the situation.

I went up to my room and sat on the bed. I took the photos out of my pocket. There we were – this Parisian man I was now entirely repulsed by, and me. I didn’t want to look at them anymore, but I wasn’t able to throw them out. So I hid them at the bottom of my suitcase.

When I got back home, I hid the strip of photos in a box where I kept secret mementos. The Paris man emailed me almost every day – more poetry, more references to my golden hair and inside jokes about being my cowboy. I responded for a little while, and then stopped. The romance had faded. I was no longer in Paris. And I no longer needed the affirmation of a man I was actually kind of grossed out with, no matter how sweetly he talked to me.

I don’t know what happened to those photo booth pictures. At some point, my parents emptied out my bedroom in their house, and they probably threw away that box of little treasures.

And even though I was entirely disenchanted with this man in the end, I still love that I met him. It’s just a perfect story; a perfect scene in a 19th century novel. Two lovers meet in the rain, in the Luxembourg Gardens, and have a whirlwind Paris romance – three weekends of making out all over the city, culminating in a single strip of photos.

At first I just laughed at Leonard, aka OKCupid user “Iwntmyjewwifenow.”

And then I realized I couldn’t stop thinking about him. I mean…he was just so weird. His erratic capitalization and use of punctuation suggested someone who was at least a little nutso. So I decided I had to meet him. It would make a fantastic blog post.

I had previously messaged him to tell him I would never be interested (because I’m an asshole who gets off on being rude to people on OKCupid).

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But I ate my words and sent him the following message:

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I knew it would resonate. It was just the kind of creepy sappy language that he used all over his profile to try to catch his “Jewish best friend on fire for life.” And I was correct. He responded.

First he immediately sent me his phone number because he couldn’t “access OKCupid from [his] home computer.” I did not call, but I told him he could text me. But no. That wouldn’t work for Leonard.

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Who doesn’t own a cell phone? Like, even a flip phone or something?

Anyway, apparently Leonard doesn’t. So we kept messaging back and forth instead. He told me his ex quit smoking for him, and he hoped I would, too. He reminded me that he had no job. Informed me that he lived with his parents on the Upper West Side. He asked me if one day “when we both have money (very soon for us both I hope)” I would move to the suburbs with him. I ignored it. It was weird, but I had had some idea of what I was getting into when I messaged this guy.

My profile says I’m a writer. He asked me what I wrote. I told him I was working on a book – his response?

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Oh, of course. A book on tickling etc. Who hasn’t written one of those?

And then this, out of the blue:

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He started and single-handedly sustained a very long conversation about where our parents were born, where our grandparents were born, what our parents did, what our grandparents had done. It was, obviously, stimulating, but I decided to change the subject.

“Now, not to be rude,” I asked, “but how do you expect to have a family if you have no job and live with your parents?”

He ignored it at first, so I asked again. And then this was his response.


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Oh, of course, you’ll move in with me!

And is the “short” comment supposed to be an insult? I mean, I’m cool with being tiny. I like it about myself. But…what the fuck?

At this point, I was beginning to doubt that I could follow through with actually meeting this man. I can handle a lot, especially for the sake of the blog, but I was starting to think that Leonard would probably tie me up in a basement somewhere and talk to me about how his grandfather started the Port Authority. And then these lovely messages cemented things for me.

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YES. “I believe I will love you” and “I don’t want to wait forever to be a dad, but we don’t have to make it happen on the 1st date either.” In the span of about a minute, Leonard had already declared his inevitable love for me and told me that he couldn’t wait to knock me up with a little Jewish baby on fire for life.

And that was too much, even for me.

At that point, I knew this could only end with me tied up in a basement. I sent another message saying that everything was getting too creepy and I couldn’t do it. He sent a few more begging me to reconsider and telling me that “yes I want to be a dad like yesterday” but that he’s much better on the phone, so we should talk. I refused.

So, Leonard didn’t get his Jewish best friend on fire for life. I didn’t get to write about what would definitely have been the weirdest date I’d ever been on. But I still think I made the right choice – even though it was tough.

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This guy’s message said “Be open minded about my age.” Note: actually 51. AKA, 5 years younger than my parents.

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And don’t forget this message (the fourth he sent me, even though I didn’t respond to any of them).

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Last week, I met a guy at my local bar. He was attractive enough, but mostly smart and interesting. He liked opera and contemporary fiction. He didn’t like disposable Ikea furniture. We talked about deep cultural stuff for a while, and it was totally fun. He was with a friend, however, who was fucking annoying, so I soon left. Plus I was pretty drunk.

Halfway home, I decided to turn around and go back to give him my number. Why not? I did, and he quickly texted to give me his.

Over the next few days, we texted back and forth. I knew that he was a smart guy, but his texts made him look like an idiot. He used “u” instead of “you” and disregarded punctuation completely. I know that’s a silly thing for me to care about, but it drives me crazy. Just because it’s new technology doesn’t mean all rules of English go away!

Against all my instincts, I met up with him for a date anyway. It was fun, actually. But he looked older than I had noticed in the dim light of the bar. I mentioned a couple of times that I was 24. He never countered with his age, which was kind of weird. I knew he was older than me, but not by how much. Finally, at the end of the evening, I asked him how old he was. “43,” he said.

Ok, we all know I like older men, but twenty years? That’s just too much. I texted him later to say that I’d had fun, but I should probably stick to dating people closer to my own age.

Last summer, I went to visit a friend in Nashville. One night, she had to work, so I went with her friend to see another friend’s band play. Ok, sounds kinda cool, right? Except they were playing at the Hard Rock Cafe. In Nashville, the city of awesome indie music, I had to go spend an evening at a lame music chain.

The music was terrible. Amateur bands are hard to listen to when your friends are the ones playing, but when it’s strangers? Really, really bad.

I tried to make the best of it. I drank several glasses of ($6) rail bourbon and flirted with the musicians. One was probably in his late thirties and was a drummer for one of the band. He told me that he was Swiss and lived in Brooklyn (of course), but he was “on tour” with his band for a few months. Playing for thirteen people at the Nashville Hard Rock Cafe.

Anyway, I got super drunk, and decided to go home with him – to the place where his band was sleeping, in someone’s basement. The highlight of the evening was that his band had picked up a mason jar of peach moonshine (the real, illegal deal) in Virginia that was one of the best things I’ve ever tasted.

We took our moonshine onto the back porch and started making out. He told me that he had a girlfriend in Brooklyn, but she understood that “what happens on the road, stays on the road.” Very classy. But not my problem. Then he decided to go down on me – right on the back porch. I was drunk enough to let it go. Who could possibly see us on the back porch, anyway? The lights were off, right?

At some point, I pulled him up from in between my legs and told him we should take things inside. He sat down in the chair next to me.

“Actually, you should probably go home,” he said. “I have this weird rash…”

I was kind of taken aback. Ok. So you let me come back with you to some strange house, eat me out on the porch, and THEN tell me about your rash? And send me home? What???!

At that point, it was three in the morning. I called my friend.

“I’m so sorry, but could you come pick me up? I’ll explain later.”

While we waited for my friend, we sat and talked for a while, about life, as if he hadn’t just been all up in my lady parts and then disclosed something totally weird. I drank some more delicious moonshine. And then, finally, my friend got there, and I left.

If you’re out there, rashy friend, I hope things have cleared up. And thanks for the moonshine. I should have stolen it.

The second time I was hospitalized, I had a therapist who I really got along with. He was smart and funny and I kind of had a (harmless, obviously unrealizable) crush on him. He was a redhead, although his head was shaved. I really liked the red hair on his arms. I know that’s weird. I feel weird even sharing that.

Anyway, a couple of months ago, he found me on OK Cupid. He sent me a really smart, really articulate message. I wasn’t positive, but I was pretty sure it was my therapist from the hospital. I responded, to clarify, and it turned out it was him. He was embarrassed, and remembered me, upon prompting. We made sure that, ethically, things were straight – it had been over two years since we had been in a patient-therapist relationship, and it had been a short, fairly inconsequential relationship, at that.

We emailed back and forth for several days. We had a crazy amount in common – we were both classically trained singers; we both were really interested in mental health. I don’t remember what else, but we were pretty much sure we were soulmates. We also had great email chemistry. He was a workaholic, so, late one evening, I decided to meet him at his office and hang out.

We stayed up until two talking. It was so much fun. Our email chemistry translated to real life, and we just had a great time. He was a total know-it-all and had crazy grand aspirations. At various points in his life, he had wanted to be pope, a rock star, and, now, he wanted to be the next Tony Robbins. But he was also a former fat kid who had been bullied like crazy, so I was completely endeared to his transparent desire to show them and feel brilliant. Anyway, we immediately connected. We both acknowledged that we were obsessive about being excited about meeting new people we liked, and hung out twice more that week. We talked about really introspective things and emailed all day and it was just, well, fun.

There were some weird things, though. He told me that he went running with one of his patients. While that’s not an ethics violation, strictly, it’s pretty on the edge. I mentioned that to my therapist, because it raised my hackles, and she definitively agreed. It was weird bordering on inappropriate, and a big, unnecessary risk to take. He and I had both discussed our mutual love of intimacy with another person, and he had mentioned that he had no relationship with his family. I got the impression that, not only was he careless, he was also kind of exploiting the intimacy of a patient-therapist relationship for his own lonely gain.

He also made me insanely insecure. Like, I felt like a crazy person. I think his know-it-allness, the 12 year age difference between us, and his general obsession with being a therapist (to the point where he kind of therapized me) created this very strange power dynamic between us. He was very sensitive, so there were a couple of times that I said something and he was wildly insulted and I had to explain myself and apologize like crazy. Sometimes he would email me every minute, and sometimes it would be a day. There really was no reasonable trigger to my insecurity, just the bizarre dynamic made me crazy.

I found myself being super, super needy. I’d send him emails asking if he actually liked me. I asked why he liked me. I asked if he just wanted to sleep with me. I wanted to see him all the time. He was super, super understanding of it – basically encouraged the behavior.

But I was pretty excited about it. I had this great connection with this guy who totally enthralled me. I told my friends about him, which I never do. He actually reminded of my one great love in life – a passionate, crazy, insecure writer who always kept me on my toes. The therapist history between us was kind of intriguing. And our chemistry was just so good. I didn’t really see the insecurity and power imbalance until later. I did see the red flags, though, about his professional ethics.

More red flags: we only ever hung out in his office. We even had sex on his office couch. Yes. That’s right. The place where his patients sat and bared their souls was also a place he was totally comfortable having sex with someone. It was just a little weird and even kind of exciting until I told my therapist about it and she was way, way skeeved out. Then I realized that, yeah, it was kind of fucked up. Even though he was a workaholic who barely left his office, there is a place for everything. And a not-place for some things.

The second week we were (obviously) dating, he told me that he wanted to label our relationship as a “developing friendship.” That made me really upset, partially because he made me needy and kind of nuts, but also because we clearly were a developing relationship and it insulted me that he wasn’t willing to call it that. But he appeased me by telling me that he could see it developing into a relationship, but didn’t want to label anything too quickly. I went with it.

A week or two later, we again discussed what our relationship was. I want to emphasize that it wouldn’t have been such a big deal if it hadn’t been such an intimate dynamic. It’s hard to describe. We talked about really intimate things, and our dynamic was just really close. We were also sleeping together, obviously. And had discussed things like whether either of us wanted kids or whatever. It was relationship behavior. So I was really hurt when he again said that he wasn’t willing to think of what we had as anything more than a developing friendship. I felt misled. I went so crazy on him that he went from “Let’s be friends” (to which I replied, “I don’t think I can just be friends”) to “please don’t contact me again.”

I cried for a night and got really wasted and then woke up the next morning feeling totally, totally fine. Out of his orbit, I could see how fucked up our dynamic was. And how bizarre his professional ethics were. I was still drawn to him as a know-it-all, but I could also see that it wasn’t so helpful to my mental health. After my one night of freak-out, I felt all-better and good and a huge sense of relief to not have to be nuts about him. It’s always most dangerous for me to get into that obsessive place about someone, and he really cultivated it.