How My Mother’s Friend’s Daughter’s Friend’s Brother Became My Favorite Ex-Boyfriend

My mom is one of the sweetest women I know — which makes her almost impervious to the harsh realities of the dog-eat-dog world of dating. For her, phrases like "give him a chance, you never know" and "the worst that happens, you make a new friend" are blithely uttered about men she's never seen, knows nothing about, and who most likely have zero compatibility with her darling daughter.

Well, except for being Jewish. It was that ineffable qualifier that prompted her — without a second thought — to give my number to her friend Natalie for her friend Sheila so her daughter Cathy could pass it on to her friend Marcy for her brother, Morty. 

My mom didn't get why I was annoyed. "You gave out my number?" quickly escalated to "You gave out my number to a guy named Morty?" What did he look like? How old was he? What did he do? Mom didn't know; it had never occurred to her to ask. Why would it? Morty was Natalie's friend's daughter's brother. Why wouldn’t I want to meet him?

I have been on a few blind dates, mostly because I quickly discovered that "Jewish" and "single" were pretty much the only criteria being applied, resulting in the disquieting realization that my friends obviously found me less attractive than I'd thought.

But with my mom, it was different: This came out of the blue, from a woman who, though she had never previously betrayed any anxiety about my dating life, probably should have been a bit more interested in the qualities of a future son-in-law brought to the table.

"Morty" quickly became "Morty, the Short Balding Accountant," because, after all, my mom couldn't disprove it. (It was at this point that she said, "The worst that happens, you make a new friend" to which I, a beleaguered junior lawyer at a soul-sapping Manhattan law firm, snapped, "I don't even have time to see the friends I have!")

Still, she must have sensed my flexibility on that point, seeing as the bar for "new friend" had recently been satisfied by a guy I'd agreed to meet for dinner based on the fact that he'd seen me on a plane and eavesdropped enough information to get my phone number through my law school alumni office.

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If Plane Stalker could get the nod, I guess I could make time for Morty, who may or may not have been a short, balding accountant. Besides, now it wasn't just about me, or my mom—  now my actions had consequences for Natalie, Sheila, Cathy, and Marcy, too. For the sake of them, I figured it couldn't hurt. I awaited his call.

And awaited, and awaited — what, this Morty was too busy to pick up a phone?

A week went by, then two; thoughts of Morty were lost in piles of due diligence binders and all-nighters fueled by Diet Coke and take-out.

In fact, I was so close to the edge that when a long weekend suddenly opened up I impulsively decided to take an impromptu trip, just buy a ticket and get the hell out of Dodge. I was trolling Expedia, deciding between Palm Springs (where my Canadian parents flee every winter) and Sweden (where I used to live) when the phone rang.

"This is Rachel," I said, in my best lawyer voice.

"Hi, this is Morty," he said, snapping me back from daydreams of strapping blond Nordic men. Swedes are very attractive. "So, you're Cathy's friend?"

As it happens, I was not Cathy's friend; the last time I'd seen Cathy was in 1987 at summer camp, where she was the drama counselor. I remembered her yelling at me once during rehearsal when I ran offstage mid-scene because someone had walked in with a pizza. Was Morty under the erroneous impression that someone in that crazy set-up chain actually knew me? Yikes. Maybe he didn't actually know that he was calling his sister's friend's mom's friend's daughter. If so, he was already one up on me.

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I explained the connection. Awkward silence. Somewhere in there floated the silent acknowledgment that our families thought we were really big losers. Change of subject. "So, you're working late." (It was 9:00 P.M.) "What are you still doing at the office?" Only now does it strike me that he thought he'd be able to just leave a message.

"I'm deciding where I should go tomorrow," I said. (It was Thursday.) "What do you think, Palm Springs or Sweden?"

There was a small silence, and then Morty made the mistake of asking me to elaborate, listening politely as I launched into detailed particulars ... and kept going.

Somewhere during my near-monologue, I remember thinking that, wow, Morty the Accountant seemed cool; I wish I could remember the three words he got in edgewise to give me that impression. I found out later that he called his sister immediately after and told her never to give his number out again.

I didn’t know that, of course, so when I returned from Palm Springs I called him, and we agreed to meet.

He offered to pick me up from my building (classy), where I made him wait in the lobby while I frantically tried on outfits (less classy). Maybe my mom was right, I clearly needed help.

As I rode down in the elevator, I felt that familiar bubble of pre–blind date excitement building, equal parts hope and possibility right before you meet someone, when they could still be anyone, including someone great. But over ten floors, I steeled myself: He seemed nice, sure, but the odds were slim that he'd be cute.

I stepped out of the elevator. There was a guy sitting patiently on the couch, waiting. He stood up and smiled, hand out. I shook it, saying hi, but inside my head, I was yelling things like He's cute! He's tall! He has hair! After all that, Morty was a babe!

We stood there, smiles a bit more genuine, possibly out of relief. "I was thinking we could go to the Hudson," he said as we walked out, sounding faintly pleased with himself. The Hudson Hotel had opened less than two months before, and it was the current hotspot du jour, complete with the obligatory celebrities and models. Great date place—if you were a celebrity or a model.

"Don't you think we'll have trouble getting in?" I asked, brow a-furrow. Morty looked at me with faint annoyance.

"I think it'll be fine," he said, with the air of someone who had been many times. Our first power struggle. Fine, get kicked out of your fancy bar, hotshot, I thought. Sometimes I am competitive.

We walked over and sure enough, there was a line, and the snippy guy with the clipboard told us that they were "at capacity." I willed my face not to look smug; the look on his face suggested that I did not quite succeed. And so we were left with a slightly strained silence and the awkwardness of finding somewhere else to go. First dates should never include travel time.

But travel we did, hailing a cab downtown, trying to drum up a destination.

We finally settled on Fez (my suggestion), a flickery, middle-eastern lounge with low couches and swingy, beaded curtains. We sat down, ordered drinks, and, finally, started hitting it off — especially since he'd arranged to have food put in front of me and I'd pointed out that the girl at the bar was totally showing her thong.

More drinks were ordered. My smile became a tad goofy. Hi Morty! You're fun! He was smiling, too. I got a little chatty. Did he know that I'd written a book during law school? That I'd recorded a pop song while I was in Sweden? That my sister was visiting because it was my birthday? It was my birthday!

It's true, I had turned twenty-eight somewhere between the thong and the third drink, and I proudly informed Morty that the real party was tomorrow at some bar in Soho. Our names were on a list. Morty, that denizen of the Hudson, seemed suitably impressed. Then he whipped out his phone and found my book on Amazon, showing off his pre-Blackberry technology. It was the year 2000, and now I was impressed. Morty was cool! And cute. Hi Morty!

Suddenly, the waitress appeared — with cake and a candle. I looked at Morty. "Happy twenty-eighth, birthday girl," he said, grinning, as my heart did a little flip.

We ended up at a diner at 4 A.M., convulsed in laughter and not even because we were drunk.

It was 5 A.M. when we caught a cab back uptown, and between the cake and the company, I was ready for the kiss. Open body language, the artful tilt of the head, city block after city block — nothing. That Morty may not have been choosy about his blind dates, but he knew what he was doing.

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The next day I got an e-mail wishing me a happy birthday, and a phone call later to say it in person. On Monday he e-mailed to make a plan:

TO: Morty
FROM: Rachel
My mom's been busy on my behalf—I’m seeing Shlomo Feingold tonight and Seymour Hirschenbaum tomorrow.

TO: Rachel
FROM: Morty
A hundred bucks say Shlomo and Seymour don't get in a combined twenty-five words of conversation.

I was no longer drunk, and Morty was still funny. A good sign! My heart did that little flip again. Or maybe it was my stomach — Morty had fed me well.

I consider it emblematic of our relationship that on our second date we saw Dude, Where's My Car? We were giggling as we left the theatre, still high on dumb humor and sitting next to each other in the dark for ninety minutes. I seriously almost grabbed him right there, but we had the good manners to wait until we got to a bar.

Is there anything better than the googly-eyed look on someone's face just before they kiss you for the first time? I can still remember. Champagne and butterflies. There's nothing better.

I feel a little guilty leading you on like this since I know how it ended, namely three-and-a-half months later with me whipping a beanie baby across his apartment. (Drama!) And even though I know it's for the best, we're better as friends, etc., etc., etc., it does make me sort of sad as I relive it in my head, and now on paper.

My mom was so proud of herself. As she should have been — she had set me up with a terrific, terrific guy, however inadvertently. But "terrific" doesn't necessarily mean "right" — and when it's not right, it has to end at some point. So, on we go.

I can still remember sitting on the counter in his kitchen as he put our Chinese takeout on plates (so fancy!), looking at me and saying, "For the record: beautiful eyes."

I can remember him so proud of himself because he'd looked up my name on Napster and found a song called "Slut Named Rachel." I can remember sending him e-mails with subject lines like "Everything's Coming Up Morty!"

More than anything, I can remember the laughter — doubled-over, can't-breathe, stomach-hurting laughter that flared up over e-mail, on the phone, and frequently in bed, though now that I think of it my occasional habit of cracking up uncontrollably may have ruined the mood a few times.

Recently I found an old e-mail, "Top Ten Reasons Why I Haven't Heard from Morty the Day Before Valentine's Day," an excuse to make fun of his near-obsessive fastidiousness ("#7—You accidentally touched the pole in the subway and are still washing your hands furiously").

That was a joke, like my Valentine's Day gift: the full "Slut Named Rachel" CD, special-ordered. At that time we were at the midpoint of the relationship, but it had all gone at warp speed: By the first few weeks we felt like we'd been together forever and by the first few months we were already acting like it. Comfortable, yes, but not exactly ... hot.

And so ...beanie baby. It wasn't because he'd done anything bad — he didn't cheat, he wasn't mean to me, he kept me well-fed. I would almost have preferred that, to have something to blame. The truth was far worse: He just didn't feel the same way I did. (How's this for shorthand: I said something like, "You make me melt," and he got all quiet. Ouch.)

Everything about us that was so great—the laughing, the goofy hijinks, the private jokes—well, it just wasn't enough.

I railed at him, tearfully; didn't he know what he was letting go? He knew — that wasn't the problem. The problem was that he was still doing it.

That part I couldn't blame on my mom, though she tried her best to comfort me when I called her on the phone, hyperventilating. Every hour. On the hour. Yeah, we've all been there. That part sucks.

But the point of this story, really, is about the part that came after; that is to say, why the part that came before — the breakup and the hurt and the puffy eyes and endless playing of sad songs — was worth it. It was the part before the before that made the difference. And he knew it, too.

On our third date, the one with the Chinese takeout, Morty stopped and said to me, "If this doesn't work out — me and you — can we make sure we stay friends?" He immediately apologized for talking about the end when we were just beginning, but I thought that sounded like an awesome deal and the best kind of compliment. I agreed, immediately.

A few weeks after we split, I ran into Morty at the airport (seven pounds lighter, thank you, breakup diet!).

It was good to see each other, if awkward, and we said we'd be in touch. And, we were. I honestly can't remember when it went from awkward and weird to telling each other about our hilarious dates and trying to set each other up, but it did, and somewhere along the line we did stay friends, great friends, the kind who all your friends meet and then want to set up with their friends. The kind of friends who have history, and a whole other history piled on top of it.

A few weeks ago, my mom came to town, and I made reservations for dinner so that she could meet my best friends, Morty included.

She loved him.

“Meeting Morty—Or, How My Mother’s Friend’s Friend’s Daughter’s Friend’s Brother Became My Favorite Ex-Boyfriend” Copyright © 2007 by Rachel Sklar excerpted from "Have I Got A Guy For You": What Really Happens When Mom Fixes You Up, edited by Alix Strauss, Polka Dot Press, 2008