“Maybe it’s better if you sleep in the living room…”

He said it with a slight of anger. Unfairly directed towards her. Mostly, he was angry at himself for letting the night end like this.

It was their first date, and he knew within the first 5 minutes that he could never love her.

Sometimes it took longer to come to this conclusion. He remembered a cute blond from 5 years earlier when he first moved to New York City. She was a really good kisser.

On their third date — a quick coffee rendezvous before her overnight nursing shift — she showed up wearing no makeup at all. Now he couldn’t stop staring at her cankles (it’s when your calves and ankles seem to fuse together with no apparent transition) which he hadn’t noticed before.

Still, it wasn’t until she made the same bad Simpsons joke that she made on their first date, that he realized that he would never see her again.

There was something freeing about that moment. Knowing that there’s nothing left to be anxious about. No reason to pretend to be someone else, or to try to present some polished version of yourself.

Not caring is a powerful thing.

He kissed her goodbye outside of the hospital and walked away with a feeling of excitement about the next cute girl he was going to meet.

Maybe someone with dark hair this time.

He’d respond to the first text from her, but not to the next two. He didn’t feel sorry for ignoring her. After all, he didn’t care.

He always hated when ex girlfriends said he was a nice guy. Not because he hated being nice, but because he knew that he was only nice when he cared.

He must have cared a lot of the time.

He remembers when he was kissing a girl while waiting for the subway in Brooklyn. She had a shaved head, but the cutest face and softest lips he’d kissed in a while.

Sure, he had just spent 4 hours with her, where he learned all about her ex boyfriend, and how she was kicking a moderately serious drug and alcohol addiction (which she blamed on him), but she was a solid 9.

They were still kissing when the subway doors to her train opened, and for some reason he stopped kissing her to say…

“Oh wait, you don’t want to miss your train.”

She got on without looking back at him.

She answered his next text with a one word reply. And then, with no reply at all.

He wondered at what point she had realized that she would never love him.

He spent the next few days kicking himself for being the typical “nice guy.”

What would a “dick” do in that situation? He’d probably keep kissing her and make her miss her train. He’d probably tell her to skip meeting up with her friend, and invite himself over to her place instead. He’d probably… actually get laid.

His college roommate once said to him — “when in doubt, there is no doubt.” That ended up sticking with him through every relationship after. A rather debilitating philosophy to live by.

And yet, doubt didn’t stop him from dating a girl he met at work for over two years.

They were seeing each other for about a month when she said “I love you.” He thought it was too early, but he would go on to do the same exact thing to someone else four years later.

He was still inside of her when she said it. He had just kissed her neck softly, breathing heavily as he let his weight drop on top of her.

There was a moment of hesitation when he finally said “I love you too.” She smiled. He buried his face deeper in her neck.

That night was the first time he made her cry.

They were sitting together in her little red car as she was getting ready to drive home when he decided to tell her what he really felt — or didn’t feel.

He said something about not being ready. That it was in the heat of the moment.

“That’s kind of fucked up” she said after a few minutes of silence.

“I’m sorry” he responded under his breath.

Three days later, he caught her looking through his texts.

As they sat side by side in the hall outside of his apartment so that his brother couldn’t hear them arguing, he thought about ending it with her.

One month later, he said I love you again — this time, with a little more certainty.

In the two years that followed, he was never really sure if it was true love. As with many subconscious thoughts, these tended to come to the surface when he was showering. He began to associate the green floor of the tub with a sinking feeling of doubt.

He cried when she moved halfway across the country for a dream job. They tried the long distance thing, but they both knew that their feelings were beginning to fade.

One week before they decided to take a break, he kissed a girl on the dance floor of a bar in Boston. She was cute, and he liked touching her soft arms as they danced.

She was wearing a silky green dress, and he didn’t feel bad when he let her press her perfectly round butt against his jeans.

He didn’t feel bad when she turned around and squeezed him tightly as they both leaned in to kiss.

As his tongue swirled from her mouth to his, he thought of the girl with the little red car, but only for an instant.

When he came back from the bathroom, feverishly looking for the soft skinned girl in the silky green dress, she was gone.

A week later, his girlfriend suggested that they go on a break. A feeling of relief washed over him. He was free.

He thought of “Friends.” He knew that she would never be his Rachel.

“I don’t believe in breaks. To me, a break is a break up…”

She backpedaled. He didn’t.

No more doubt.

It would take him 4 more years of dating and one more bad breakup (he never had a good breakup) to find a woman with whom he felt no doubts.

He met her online, like most of his romantic interests. Dating was more predictable that way — like when he used to work in sales. Message X amount of women, get Y amount of responses, and schedule Z amount of dates, accounting for people that would cancel last minute.

It was easier in the winter — people are lonelier when it’s cold and the sun sets too early. Everyone wants to be the little spoon then.

He met her in the summer though.

Their first date was the best first date he had ever gone on.

She told him to bring his guitar. They sang for hours, sitting on the outdoor terrace of a bar on West 51st street. An older couple stopped by to listen to them harmonizing “I’m Yours” by Jason Mraz.

“You two are adorable! How long have you been together?”

Her face got red.

“This is actually our first date” he said, with an awkward smile.

“Really? You look so comfortable together, I thought you guys might be married.”

After the couple left, he pulled out a joint from his guitar case.

“You said you smoke, right?”

“Umm, okay sure…just a little bit please” she said with her cute foreign accent.

On their third date, she invited him back to her place.

In her dark room they took off their clothes, and melted into her soft bed. Their kissing wasn’t lustful. It was soft and loving.

She was tiny and powerless in his arms, and that turned him on even more.

She slowly moved her hand below his navel, grabbing him assertively yet softly.

“Umm, do you have a…”

“Oh sorry, yeah — I have a hood.” He said, interrupting her.

“What’s a hood?”

“Oh, I’m not circumcised” he said bashfully, not knowing if she’d seen an uncircumcised penis before.

She burst out laughing, catching him off guard.

“I meant, do you have a condom.”

He sunk his face below her chin, pressing his lips against her chest as he chuckled with embarrassment.

“Oh god. Sorry, yes. I just didn’t know if…ugh, yes I’ll get it.”

After they had sex, he was laying on top of her in between her legs. She was sitting up with her back propped up against a few pillows.

He kissed her softly, and pulled away still looking in her eyes.

As he studied her pretty face, for the first time in his life he thought to himself “I’m going to marry this girl.”

From that day forward, they were inseparable. Some days they would spend every waking and sleeping moment together.

He remembered lying lazily next to her one sunny Sunday afternoon, with her fingers running through his chest hair, feeling completely intoxicated and thinking — “this is better than any possible high that you could get from a drug.”

Three weeks after their third date, he officially asked her to be his girlfriend.

One week after that, he was ready to tell her that he loved her.

It happened right before she was about to leave for a one week trip abroad.

They had been in bed looking into each others eyes for several minutes without saying a word, and that’s when he decided to do it.

His heart started to beat faster. He ran through the words in his head again.

“Hey listen. I didn’t expect this to happen so quickly, but I’m really starting to care about you. You’re really sweet, and I’m already starting to feel that… I love you.”

She looked away, staying silent.

He didn’t know then, but this was the first time that she felt doubt.

She told him that she thought she loved him, but she wasn’t sure — she had never really been in love before.

Two weeks later, she told him that she did love him.

He was too blinded by love to recognize the pattern — to remember that night with the girl with the little red car.

She continued to tell him that she loved him, but would eventually break his heart two weeks before their one year anniversary.

“When in doubt there is no doubt.” He thought back to his college friend, who was now engaged to his girlfriend of 7 years.

It took him 30 years to find the girl that he wanted to end up with, and it took her 5 seconds to say: “I think we should break up.”

“Better to have loved and lost?….fuck that guy” he thought, wiping away tears as he rode his bike home from work the next day.

Six months later, and two months after they stopped talking, he was laying in bed staring at the ceiling as he could hear the girl that he met that night — the girl that refused to even kiss him when they got back to his apartment — the girl that he knew he could never love — start to doze off.

“You sure you don’t want to sleep in the living room?”

She didn’t answer.

Maybe he’d have to wait another 30 years.