ACCORDING TO my most recent first date, the scent of relationship material oozed from my pores. Judging by the person-shaped hole he left behind as he ran out of the restaurant, it also worked as a man repellent.

Unfortunately he was just the most recent in a string of dead-end possible matches. I’d hoped talking it out with my best friend would gain me some sympathy. I could not have been more wrong.

“You got an It’s not you, it’s me dumping via text? Seriously, that’s like a step above a Post-it,” my soon-to-be-ex-best friend Naomi mocked.

“Stop comparing my life to Sex in the City. I am not Carrie and you are not Miranda,” I snapped.

“Can’t I be Samantha? Besides, whether you want to admit it or not, you are the male Carrie, just not as well dressed.”

She had a point. I’d always been a total romantic, and as much as I’d love to be the tough city guy, it wasn’t me. I’d never been a snazzy dresser—stereotypes be damned. If Naomi hadn’t helped me select my wardrobe, I’d only be seen in khakis and jeans. It wasn’t like I was hideous or anything—tall and lanky with dark hair, which I kept short due to its tendency to curl, and light brown eyes—I got my share of second glances. I might not have been rocking a six-pack, but an active enough lifestyle kept me pretty fit.

Break-up-by-text guy was actually named Kevin. He had white-blond hair and startlingly dark brown eyes. The contrast was stunning. I met him at the grocery store, near the cucumber display, and spent an hour talking and shopping with him. By the time we got to the checkout, we had a date scheduled for the weekend. With that kind of meet-cute, I just knew we were destined for a happily ever after.

Our date was romance novel–worthy. We had dinner at a trendy restaurant in Brooklyn; there was no shortage of conversation. He laughed a lot—the real kind where your eyes crinkle up at the side. Sometimes he even let out a little snort; I found it charming. Charming enough to ignore his wandering eyes. Maybe he just liked to be aware of his surroundings.

After dinner we went for a walk and found a small fall festival. We played games and ate cotton candy. We even purchased two pumpkins and made plans to carve them on our next date.

I lived close by, so he walked me home. Of course I invited him inside for a beer. That led to a discussion of lagers versus ales and a decision to go out for some beer sampling sometime soon. Two dates planned—oh, this was so going somewhere! I leaned in to kiss him good night; he tasted of Tic Tacs and beer. His eyes fluttered closed, and he ran his hands over my shoulders. As he pulled me over him, I straddled his lap, and he ground his cock against mine.

“Wait, wait.” I pushed away slightly, putting my hands on his chest. “Let’s slow things down.”

He ran his fingers through his hair and took a deep breath. “Okay, but you need to get off my dick.”

Awkwardly I lifted my leg over and sat back on the couch. He rose, visibly trying to calm himself, and took another pull off his beer.

Once he seemed more in control, he turned to me and took my hand. “Walk me to the door?”

He kissed me again before he left. The last thing he said was “I’ll text you about next time.”

I got the text the next morning: I had a fun time, but I don’t think I’m the best man for you right now. It wouldn’t be fair to start something. You’re a great guy. See you around.

I gave the pumpkin to the little girl who lived below me. I never wanted to see that damn gourd again—certainly not smirking at me through Halloween.

Two weeks later I met Craig. He worked on Wall Street and spent most of our date texting. He informed me he was not “relationship material” and stopped answering my calls.

Naomi snapped her fingers in my face. “Hello. Want to pay attention to me?” She exhaled loudly. “Seriously, Josh, what do you expect? For all your talk of a husband, children, and a white picket fence, you only go out with the players. You ignore every red flag there is. A leopard doesn’t change its spots. If you want a good guy, it’s time to change.”

We were sitting at the bar in a small corner pub. Popular with the locals, it certainly wasn’t being written up in magazines. Wood tables and low lighting allowed us privacy. A car race played on a muted TV in the corner. An eclectic group of people—and their conversation—filled the tavern.

I fiddled with the cocktail napkin on the bar while she spoke. I was a total hypocrite, I knew. I’d always dreamed of that happily ever after, and yet it was the bad boys who got my engine revving. Give me a hot guy with no interest in monogamy, and I will want him. Sad but true. I’d never date myself. It seemed it would take a miracle for me to find my happily ever after.

“Are you planning on throwing spitballs at me with those?”

Somehow while listening—or tuning out, depending on your definition—to my friend’s advice, I had managed to tear the cocktail napkin into tiny pieces, which were now balled up in a pile. It resembled a stack of snowballs ready to be thrown. I smiled, flicked one in her direction, and laughed when it got stuck in her hair. She sighed and set about trying to extricate the paper. With long nails and her tight curls, it was a lot easier said than done.

She rolled her eyes at me, kicked me under the table, and continued playing with her hair. The girl could multitask. “Hey, wise guy, don’t take your sexual frustration out on me.”

“I’m not sexually frustrated. I had an orgasm just this morning!”

“What you do by yourself doesn’t count.” She smirked. “Seriously, what are you doing? You’ve got a great job, amazing friends—” She stopped to pat herself on the back. “—my God, you even volunteer with kids. Why do you waste time with these losers? If you want a change, you need to make one.”

“Sure, I’ll get right on that.” No problem at all. I swiveled my head, trying desperately to find the waiter. I needed another drink.

Then she picked up her straw and spit that napkin back at me. A real class act.



WHILE MOST people might have been done working for the day, I wasn’t. As a real estate agent in Brooklyn, I frequently got calls or emails in the evening. Although I tried to avoid showing homes at night, I could still meet with clients to get an idea of what they wanted. For all my failure at finding my Mr. Right, I had been very successful finding Mr. and Mr. Perfect Couple their homes. I had a great sense for people and what they were searching for. Although my clients came from all walks of life, thanks to word of mouth, most of my clients were part of the LGBTQ community. I loved what I did―it gave me a chance to meet people and explore the neighborhood I adored.

The weather was turning cool. Autumn was upon us, and I knew the holiday season would hit like a ton of bricks, crushing my income along with it. Since I didn’t do as much business in the cold weather, I tried to work twice as hard in the fall to prepare. As I strolled down the quiet street, lined with brownstones and glass-fronted businesses, my phone rang with an unfamiliar number. I assumed it was a client.

“Josh Perlman,” I answered.

“Hi, my name is Ilan from Israeli Pilgrims. I was given your number by Steve Klein. Do you have a few minutes?” The accented voice on the other end was raspy, as if he smoked a lot of cigarettes.

I volunteered for a local temple youth group. Growing up I was very active in mine, and I wanted to give back. Anything that gave kids a sense of community and helped encourage strength of character was a good thing. Anyway, Steve was the director of the youth group; I wasn’t sure why he was having people call me.

I continued walking as we spoke. My apartment was just a few blocks away. “What is this regarding?”

“Well, we understand you volunteer as a youth leader. Have you heard of Israeli Pilgrims?”

Of course I had. They were a huge philanthropic organization, specializing in sending Jewish youth to Israel on a ten-day trip to discover their roots. The participants were usually college-aged, and at twenty-seven, I was way past that. Now I was intrigued.

“Yes, but I’m a little out of your age range. I think you might have me confused with someone else.”

“Oh no.” Ilan laughed. “Not as a participant—we need group leaders. Since the participants can be up to twenty-three, we are seeking strong leaders that are a bit older. Steve and I were having a lunch meeting and I mentioned that we needed someone, and he couldn’t recommend you highly enough.”

“That was so nice of him. And I am really flattered, but I can’t get away from work right now. Besides—”

“Wait—I think you misunderstand. The trip isn’t until December. It’s over Chanukah, actually. And we cover all of your airfare, hotels, and meals. You are only responsible for your spending money. In return you work with a female leader, an Israeli medic, and a tour guide to take twenty participants around Israel in a bus. The itinerary is planned. All you have to do is organize rooming and make sure everyone is where they should be, when they should be.”

Leave my job and friends for almost two weeks? No way. I was trying to figure out a way to politely make my point when Ilan said something that turned it around. “Sometimes a change of scenery can change your life.”

“I’m in.”