My first dating experience started with a crush on a girl named Tish. I told my then best friend, Al, who then asked her out behind my back, that same night. When I confronted him about it, he told her what happened. She offered me a sympathy date. We had one awkward date. It was too weird and too late.

Then I liked a girl named Baijanti. She liked me back. We had a very physical relationship. I can't really pinpoint why it didn't work out. Maybe it was a mix of us thinking we're not good for each other, wanting to explore our other options, rumors spreading around about our sexual activity... She was my first girlfriend though. She always will be.

I continued to hook up with girls, desperate for validation and self esteem. At one point at 16, I was a virgin making out with two blondes on a cruise. They asked for a threeway. I turned it down. I didn’t regret it then. Later I did. Virginity is a social construct. That story might have raised my self esteem.

I had a long fling with a psycho which I had long paid for. She would offer to satisfy me five times a day. It was like being a prized bull. After a few months, she regretted it. Who’d have guessed? [/s] The lesson here: Affirmative consent isn’t enough when dealing with a psycho. Remember this lesson. I didn’t.

At 17, I dated Bailey, girlfriend #2. Bailey was a friend of friend. It was the only time in my life I dated a friend of a friend. She was cute, Jewish and a real… idiot. I was cute, Jewish, and… way too immature for her needs. She wanted someone to marry. I wanted someone to take cute travel photos with. She cheated on me in a threeway with two guys. When she told me I fainted. It was the only time I ever fainted.

I backpacked Europe at 18 - no hookups. No dating.
Freshman year of 18/19 - no hookups. Only bad dates.
I blamed it on low self esteem. Maybe it was luck.

Sophomore year, I had a fling with a drug addicted, professional cheerleader. She taught me how to please women, which truly was invaluable. Her own looks boosted my confidence to a place it will never return. The timing was off. We were both loaded with trauma. But for a brief moment, we were there for each other. And that seemed like the most important thing. Back then.

Then the dating apps started. Tinder was released exclusively for iPhone owners. It was a fun time. Between the app and underage drinking, I had several lame hookups I’d rather not reflect on. Then I met PVD while leading a meeting. My jaw dropped at this a-mazing, colorful, fun, 5'11, fit, blonde with the squishiest body. I met girlfriend #3 while casually dating PVD. I broke it off with a tall, intelligent sweetheart to pursue a neurotic psychology major with identical interests to mine.

I’ll rewind — Coming off my peak confidence, a healthy relationship with a beautiful woman and a social life that most wouldn’t believe was possible, I saw a love of my life. She was leading a neuroscience meeting. I couldn’t imagine anything sexier. I remember thinking, “Don’t sleep with her too quick. This is the one.” After a few weeks, we started dating. I should have noticed that she had dropped her then boyfriend to be with me. I didn’t. Afterall, I had dropped a FWB to be with her.

She wasn't as into me as I was into her. That was just a pattern I was used to. It was a pattern that brought my confidence down. If you have low self esteem, try to not date people who make it worse. Here’s the pattern to look for: 1. You fall hard for someone 2. You go for it. 3. They seem hesitant to date you. But you try anyways. 4. You feel they grow “feelings” because of your kindness, maybe your sex appeal and skills. They likely even tell you how much they’re falling for you. 5. You ignore that their feelings of love relate to being treated well, not for you. 6. They destroy you.

Let’s call ex-girlfriend #3 Ann. Ann cheated on me. That didn’t stop me from loving her. Ann moved to Maryland. That didn’t stop me from chasing her. I had another year of college, filled with confusion over ex-girlfriend #3. There’s feelings that just never leave, no matter how much you wish they did. Who can deny a feeling?

The rest of my senior year I had a bunch of flings, while wanting Ann. It was a real confidence boost. A notable story was Ann 2. Ann 2 was a girl who biked over to my house for sex, 6 or 8 times, and later regretted it. Why? Cause one night, in a drunk stupor, I called her “Ann 2.” So we both knew I wanted Ann 1. There are other stories. Like failing to tell my feelings to one crush on a wild night, only to have a fantasy date, a married woman, standing on my porch at 3AM, asking to come in. But these are just fun stories. Ones I vaguely forgot.

After graduating, I went back to Ann 2. We lived for two years in Maryland, three months in Texas, then tried long distance. When she came to visit me, I greeted her with flowers and a plan to see a group of our friends. I knew from her face it was over. Later, I learned she cheated on me, and worse. As hard as it was the first time she cheated on me, this time was harder. I didn’t faint like with ex #1. I lingered onto cherished memories for years. Fainting would have been less painful. This therapist will never know the amount of emotional pain she’s caused. Which makes me wonder how much pain I caused my own flings and exes.

You might be wondering how I was cheated on twice. Cheating is rare. I’d wager it was related to my emotionally immaturity. It didn’t help that I rubbernecked, was not accustomed to gift giving, and worst, did not have a stable income. All these things add up to lack of trust. I never cheated. But, boy, reader, was I accused of it. Here’s two signs someone is a cheater: 1. They abruptly leave someone to be with you (people repeat actions) 2. They accuse you of cheating (they’re projecting their own intentions). I’m digressing.

I dated a Vietnamese girl for a few months. She was later diagnosed with bipolar issues, but was only ever sweet to me. We were not compatible. I had a fling with Pam, a beautiful, tall, funny, wealthy, extroverted, politically woke woman, who happened to also have a movie theater and special fridge for international craft beers. These and other dates came during the period I was in love with someone who had long moved past me. Pam broke it off with me on my birthday. I don’t blame her.

I moved overseas. I studied and had a childlike crush on a classmate. She downplayed a relationship with her “friend” and let me take her out. She was engaged within 6 months of our date. Come to think of it, most of the girls mentioned above are now married. I’m not.

Around this time, I averaged a few dates a week. I enjoy dating more than most. Dating is what you make of it. It’s not always an interview. It can be like hanging out with a new friend. Just don’t add pretenses of wanting X, Y, or Z, especially if X is a hookup, Y is a ring and Z is happily ever after. Be easy. Think: wine at a park, a walk to grab pizza, rounds of pinball. Whatever you enjoy. The point is to be fun and comforting.

Men, remember we live in a sexual-assault ridden world. Many need a safety check from a friend and an evacuation plan just to go out on a date. By your late 20s, finding dates through classes and hobbies becomes rare. You know, because you’re not in school anymore.

Dating is not like sitcoms. After attending hundreds, maybe even a thousand concerts, I’ve never once picked up someone at a concert, music festival or rave. I never slid into Jerry’s apartment after a date to talk about their obscure traits. I have met dates at networking events, the beach, cafes, bars, extracurriculars, volunteering and other places. But mostly online. I don’t know if soulmates are real, but I do know meet cutes are not.

My worst dates involved driving mismatches home with thoughts of, “How did I get here? Maybe I’m what Phoebe from Friends would call a simp.” One girl left me alone at a club after our initial chat, put two drinks on my tab, then, at the end of the night, asked for a ride home. One girl drooled profusely mid-sentence and never acknowledged it. I saw the drool hit the table. No, “Excuse me.” She just kept talking. I had one date who kept talking about her nephew. After a few hours, I realized she was hiding the existence of her son, thinking “nephew” was a sly replacement. One made a plan online with me to go out. Instead, I arrived and we just watched TV with a gay couple, who surely wondered why I didn’t leave as soon as I saw her IRL, without filters. One date asked if I wanted wine. I said, “No. I’m driving.” She bought wine anyways. Check came. “How should we split it?” “I’m happy to get the food. I think you should get your wine.” After a death stare deadlier than Cyclops/Superman’s, I paid, knowing I’d never see her again.

Most dates were fun, even without chemistry (chemical bonds?). I had one date who argued with me about politics right away. We were both left, but she was much further left, and wanted everyone to know. I told her I’d get the bill and she could leave whenever. She left without finishing her first drink. I laughed and enjoyed my night. I had one date who asked to eat my discarded, fried shrimp tails. I didn’t mind. I thought it was bizarre, but cute. I’ve had massages on dates and have been asked to lock arms and hands way too early for my comfort. I’ve partied with dates, and stayed friends with people from those parties, even though we don’t remember the date’s name. I was once serenaded by a large group of strangers, who must have sensed the first date energy. I had a guy named Jenkins give me a wad of cash to take my date out, because we were cute and broke. I’ve found money on the floor. I’ve wound up playing bongos at 5am on a Vegas rooftop with a guy dressed as the devil, wondering, “Did my date leave? Oh well!” I don’t remember these girls, but I remember the experiences.

Every once in a while there was a match. We dated for 4-6 months, then broke up. Not enough attraction, ambition, differing life goals, and a long list of unverbalized reasons that prompted the “If it’s not a hell yes, it’s a no” rule. These are the sorts of relationships I feel too used to. They’re like dating purgatory. I can name a few, “It’s not me, it’s you!”: Kendell, who yoyo’d in weight so much people didn’t recognize her the 5th time meeting her. Sharon, who felt a relationship would stifle finding a direction in life. Carla, who only wanted something physical at her convenience. Vanessa, who worried I would move back to US someday, and decided she wouldn’t ever want to come with. Neta, who felt conflicted as a Muslim dating not just any Jew, but me! Like the song Mambo #5, the list of names in my life keeps going.

They say you can date 6 people, and if you're not settled down by the 6th, you never will be.

ALL NAMES HAVE BEEN CHANGED TO NAMES I NEVER DATED.
EXCEPT JENKINS. THAT WAS REALLY HIS NAME.