Girl Walks Into a Bar . . .: Comedy Calamities, Dating Disasters, and a Midlife Miracle

by Rachel Dratch

  After only about fifteen minutes of conversation, he asked me when I was coming to visit him in California. I had to go back to Lisa at our table outside, but I told them to come join us out there and they did. He was quite forward, telling Lisa right in front of me, “I think your friend is cute.” Of course he had to check with her first on the sly to make sure we weren’t a couple—that’s the drawback of having a lesbian as your wingman.

  Only a few minutes after John and company joined our table, we had a jarring New York Moment. I find New York City to be a pretty friendly place, and to me, once you know your way around, it feels like a big neighborhood. I’ve rarely run into any “crazies.” We were sitting at the table and a man was walking by with two large dogs pulling at their leashes. I first noticed him because of the unusual dogs—they were straight-up hound dogs, a rare sighting in Manhattan. The man looked to be in his mid-fifties with a gray crew cut and black-rimmed glasses and shorts. As he walked by the table, he leaned in and, out of nowhere, screamed at us, “YOU’RE ALL A BUNCH OF COCKSUCKERS!” The dogs reared up on their hind legs and started barking like the animal henchmen who accompany the villain in a Disney movie. We were so shocked, we practically choked on our drinks, not knowing whether to giggle or “throw down.” (Not that I’ve ever “thrown down.” Which you can tell because I put it in quotes.) Then he looked right at me. He looked straight into my eyes and said, “AND YOU! YOU’RE A F***ING C***!”

  Well! That was … um … wow. Strange scenario to be in with someone you just met. We all had a shocked laugh about it. I wanted to apologize for my city the way you would for an embarrassing relative. “I swear, New York never acts like this. I don’t know what New York’s problem is—usually, New York is really nice, seriously!”

  I didn’t think John knew who I was from TV. If he did, he didn’t let on. Later in the evening, someone walking by asked to take my picture, I think, but the moment just came and went without discussion. I later found out John did know who I was but also that he didn’t have a TV. So he had a vague idea of me but wasn’t such a fan he was going to barrage me with questions: “So! Who was the worst host?”

  John was going to be in town for one more night. He walked me back to my apartment. “Am I going to see you again before I leave?” he asked me, so I invited him to come out with a group of friends who were going to dinner the next night.

  He arrived at dinner bearing bacon-flavored lip balm for all, from the food show he had attended earlier that day. This guy could be a winner. We broke off from the group after the meal and hit another bar and then he walked me back to my place. “You can come up,” I said, “but let’s not go apeshit.” The next day, John had to go to the food show to work. He had mentioned that in addition to selling wine from New Zealand, his company also sold New Zealand mussels, but the mussels weren’t selling as well. In the morning, we were joking around about how he could get the mussels to sell better. I was picturing him bounding out onto the demo area, wearing a foam mussel headpiece for a costume, with one of those headset microphones, clapping his hands over his head as the song “Y’all ready for this? ba ba bum BA BA bum, bum bum bum bum BA BA ba bum bum bum bum” played overhead. We started laughing at this vision and ended up laughing so hard, we couldn’t breathe and had tears streaming down our faces. I admit this may have been one of those “you had to be there” moments, but I registered at the time that it’s pretty rare to have a laughing fit like that with someone you just met.

  “You should come to Mill Valley this weekend for July Fourth.”

  “You’re joking, right?” I asked him.

  “NO! We’d have a blast.”

  That was too crazy for me. I had known him for two days at that point. No, I couldn’t just up and visit him in California that very weekend. After he went back, he sent me cute and funny texts over the next few days, making sure to bring up July Fourth. I thought about the holiday weekend I had planned—Shelter Island with a fun group of friends—but it was my same old deal: me with some couples, a few single ladies, and absolutely no prospects. Maybe it was time for me to take some radical action. I think another factor was a failed setup that had just occurred, where this guy and I had been e-mailing back and forth for about a month but I had been out of town so much that, by the time we were supposed to meet, he had met someone else. That was fresh in my mind regarding John, who lived in California. A few days before July Fourth, I asked John, “Are you still serious about me visiting?”

  “Yes! I’ll fly you out here.”

  “You don’t have to fly me out there.”

  “If you’re gonna spend five hours on a plane to see me, I’m flying you out here,” he insisted. “Weird,” I thought. “This must be what chivalry feels like.”

  I got on the plane, propelled by a heady mix of curiosity, adventurousness, and post—Dating Crusade, single-lady desperation. I had always had an impulsive side, which made this seem kind of crazy but not entirely out of my wheelhouse. Somewhere in the back of my head must have been the thought that No leads to dead ends, and Yes leads to possibilities. Again, hearkening back to my improv days, this was the ultimate “Yes And.”

  John picked me up at the San Francisco airport. The visit did not start off seamlessly, since I was on the wrong level and we kept having to call each other and I was saying, “I’m on level 2,” when actually I was on level 1. Already, this was not the movies. Once we connected and I got into his car, we enjoyed an extremely awkward ride back to his house. When I’d met him in New York, he was all confidence, but in the car, he seemed nervous, and that made me nervous. We struggled for small talk, with silences filling the air. Internally, I started to panic, thinking, “What the HELL am I doing here? Screw ‘Yes And.’ That’s a horrible concept!” His place was a nice town house with bachelor-pad style—not a lot of furniture, just the basics. Like I said, he didn’t have a TV. He would watch documentaries on Netflix instead. (That automatically meant he used his time more wisely than I, who have my TV on Bravo 24/7, squandering my time with Real Housewives.) We had to resort to cracking open a bottle of wine when I arrived—yes, at the extremely early happy hour of one P.M.—to ease our fear, but we ended up getting over our nerves, and I actually felt more comfortable with him as the weekend went on. Not fully comfortable—I had a baseline of nervousness that made me barely eat the whole time. This trend would soon reverse when we got to know each other better and he dubbed me The Crow for the way I picked apart my food as well as the remnants of his, leaving behind a plate that looked as if a bird had landed on it.

  John was a very sweet planner and tour guide, offering all sorts of options for the weekend. We ended up going to a few parties—one at the home of a friend of his and one that we were invited to by one of the Dartmouth Gays—an annual Pork-Off party where people competed in cooking various pork dishes. We all had to submit a “porku”—a haiku we wrote about pork. John showed me around San Francisco, a city in which I hadn’t spent much time. We stopped at the marine mammal rehab center and looked at the seals. That trip was slightly interrupted because John also worked for a vitamin company and had taken a B vitamin with a “niacin shot” when we were leaving his house. I took one too—what the heck—and partway through the marine center, my face started to feel hot. I looked in the mirror, and my face, neck, and hands had turned bright red. I was having some sort of allergic reaction to the vitamin. My bright red, burning tomato face lasted about a half hour. It was a bit embarrassing but more funny than anything else. I mean, once you’ve been called a f***ing c*** in front of someone, the bar of social awkwardness has been set pretty high.

  A whole weekend date with someone you don’t know all that well can be intense and nerve-racking and fun all rolled into one. John commented that we were experiencing the “waterboarding” of dating, and I had to agree. The next time I saw him, he had a gift for me…. He had tracked down a T-shirt that said I’D RATHER BE WATERBOARDING.

  After the July Fourth weekend, John and I
continued our long-distance, casual, fun, not-defined relationship. We talked on the phone pretty much every day. He definitely acted like he was courting me. He’d text “I miss you! Wish you were here!” I really wasn’t used to this dynamic at all—being pursued instead of feeling like the pursuer. A month later, he came to New York and accompanied me to Fire Island, where I was doing an ensemble comedy show that I do from time to time. It’s always a hit—always gets laughs—but wouldn’t you know it, on this particular occasion, the first time he was ever seeing me perform, the show completely bombed. I was mortified. I sheepishly skulked up to him after the show and had to trot out the old Second City improv line: “This is usually really funny! I swear!”

  As the cross-country visits continued, we would usually end up having a few major laughing fits together. He continued his surprise acts of chivalry and sweetness. When I went to wine country with my friends and happened to mention to him the wine we liked best, a wine I had never heard of from a tiny family vineyard, a case of it arrived at my apartment a week later. He had ice cream in his freezer called Three Twins, and when I tried it, I exclaimed, “Oh my God, this is some of the best ice cream I’ve ever tasted!” Wouldn’t you know it, six pints arrived in New York on dry ice. (Have you noticed a food and wine theme here?) He was always planning our next adventure. “Come meet me in Chicago!” he’d say when he had a meeting there. He came to Manhattan in September for a few weeks and stayed in a friend’s vacant apartment because “he’d always wanted to live in New York at some point,” but it sure seemed like he was coming east to hang with me.

  Gore vs. W

  Our relationship was perfect for two people in their early forties who lived in two different cities. We both liked doing the same sort of things—travel, food, wine, nature. I wasn’t sure that on a soul level we were connected. I don’t think either of us was, like, “I’ve found the One!!” but neither of us was too concerned about that fact. It was enough to have a fun “date” and a nice guy to pal around with. There was no pressure to think of “Where is this going?” since it hadn’t been going very long at all.

  In many ways, we were quite different. He’s a Midwesterner who was raised in a devout Catholic family and went to a small business college in Michigan that he calls “one step above DeVry.” I’m your typical East Coast gal from the burbs. John told me his dad is so devout that he goes to the church to babysit the statues a few times a week. I thought this was a euphemism of some sort—that he stopped by to make sure everything looked cool, but no—he actually goes and sits with the statues. Aside from the religious differences, though, John possesses a lot of the qualities that I had on my “list.” I put the word list in quotes so you don’t think I’m one of those women who actually wrote out a list, but the truth is I did, so in reality those quotes are a bit of a lie.

  John was funny, smart, handsome, very fun, generous, extremely thoughtful, around my age, open to meeting my friends, liked to travel—the list goes on and on. About a month or so after I met him, we were talking on the phone and something about politics came up. John made some comment that sounded a bit right wing to me—I think it may have been something positive about George W. Bush.

  “Whooooa. Hold up, hold up, hold up,” I said.

  “What is it?”

  “ARE YOU A … REPUBLICAN?!!” I nearly shouted in a shrill tone.

  Slight pause. “No. I’m an Independent.”

  “BULLSHIT!” I cried. “YOU’RE A REPUBLICAN!”

  Oh … my … God. I was dating a Republican!? HOW did this HAPPEN!!!? “OK,” I said. “Even if you are a Republican, you have to admit that George Bush is an idiot.”

  John proceeded to list some of the “good things” George Bush had done. “UGH! I can’t believe this!” I was practically hyperventilating.

  “Wow,” marveled John. “You’re really getting angry about this!”

  OK. Reel it in, Dratch. He was right. He wasn’t getting angry that I was a flaming liberal. Yes, he would call me Al Gore when I insisted on recycling. Yes, he would later soundly mock me when I actually brought home empty plastic bottles in my suitcase after we were in a place where recycling wasn’t available. But doesn’t he know that there’s an ISLAND OF PLASTIC THE SIZE OF TEXAS FLOATING IN THE DAMN PACIFIC OCEAN!?!! Deep breath. Anyway, he wasn’t getting worked up because I was a flaming liberal. Yet here I was, having a conniption fit that he was an “Independent.” (It can’t be true. I know he’s a Republican!) When I hung up, I had to give myself a talking-to. “Look, you haven’t dated anyone seriously in about five years. You’re not going to be able to have everything on your ‘list’ (again with the quotes).” But that was the thing I realized. I hadn’t even put Democrat on my list. Most everyone I know is a Democrat, with the exception of two girlfriends with whom I avoid talking politics entirely. Thus it’s kind of my own fault for not writing exactly what I wanted on the list. So I just don’t really discuss politics with John. I tried to venture there, on a topic I thought surely everyone could agree on. “I’m really upset about this oil spill,” I said. “Yeah,” he replied, “and the Obama administration waited, like, a week to really respond to the problem.” OH! YOU MEAN THE “PROBLEM” THAT BP CREATED AND HAD NO BACKUP EMERGENCY PLAN AND NOW HERE WE WERE A MONTH LATER AND THERE WAS NO SOLUTION IN SIGHT? But I didn’t say that. I noted my increased blood pressure and heart rate, remained silent, and thought, “From now on, I’ll just talk about this stuff with my other friends.”

  Meet Me on the Astral Plane

  In spite of our outward differences, John and I seemed connected on some sort of psychic level. Sometimes our connection on the spiritual plane gave me pause and made me think I shouldn’t take our connection on this plane so lightly. When I went to San Francisco the second time, we were staying at a hotel across from the food and wine fest where we were spending the weekend. When we awoke in the morning, I was aware that I had had some really bizarre dreams, some so bizarre I certainly wouldn’t have shared them. Namely, I had dreamed of a detached penis. It was the first and only detached penis dream I could recall ever having in my life.

  “I had a really weird dream last night,” said John.

  “Really? So did I,” I said. “What did you dream?”

  “Well,” said John, “I dreamed of … a detached penis.”

  Oh … my … God. I looked at him with wide eyes. “NO WAY. I HAD A DREAM OF A DETACHED PENIS!!”

  “WHAT!?”

  “YES!! A DETACHED PENIS! I’VE NEVER HAD A DREAM OF A DETACHED PENIS IN MY LIFE!”

  The penii played different roles in our dreams. In his dream, we were in a car and we were pulled over by the cops. The cop, who, because this was a dream, was of course represented by Gary Busey, was saying, “You two are in big trouble!” and he was waving around a detached penis like a weapon. He was waving it in my face and threatening me with it, and John was trying to intervene. In my dream, there was a detached penis lying on the bed and it belonged to my old boyfriend. I was wondering if I could keep it for future use or if anyone would know I took it or if I would get in trouble for that. I don’t know—both dreams involved consequences and getting into trouble and … a detached penis. Though I did minor in psychology, I can’t really crack the code on this one. Maybe if I had majored in it, I could.

  Since that happened, I would check to see if any of our dreams matched up again. When we were saying good night on the phone, I’d say, “OK. See you on the astral plane!” I didn’t see him on the astral plane until several months later, when we were on a trip together. When we awoke, I realized I had had a ton of vivid dreams that night. I mentioned this to John. “Did you have any?”

  “No,” he said. “Actually, I was awake at, like, four A.M., and I realized I left my blue fleece jacket on the plane.”

  I stopped in my tracks. I clenched his arm.

  “Oh my God! No way!” I cried.

  “What?”

  “I have chills!”

  “What?! What?
!”

  “I dreamed that I was holding a blue fleece jacket, one that really exists in my apartment, and I was offering it to you, saying, ‘Is this yours? Does this belong to you?’”

  In November, John e-mailed me to say, “I have a business meeting in Florida. You could come down and meet me on such-and-such a date. Or … Kauai, December 18–27.”

  These were some grand plans. I’d never been to Hawaii. It seemed very honeymoony. Maybe we weren’t serious enough to take that kind of trip together. If I had been in my early thirties, I would have asked myself things like “Where is this going? What are the implications of this? Is this too big a move?” But when you’re forty-three, you’re like, “Who cares? I’ve never been to Hawaii. I have fun with this guy. I’m going.”

  Kauai was so beautiful that my mind couldn’t comprehend it was real. On a hike, we would joke that we were going to look down and see an electrical outlet coming out of the rocks and realize we were just in some Disney World exhibit. We hung out on a private beach in the company of a monk seal and went on hikes through the otherworldly beauty. A truly bizarre thing was there were paparazzi on this remote nature trail following us to take pictures of … me? I wanted to tell them—“Guys! Save your energy! These pictures might fetch about two dollars on the mainland!” But other than that, all was very idyllic. Although John did manage to step on a sea urchin and we had to go to the ER to remove the pieces from his foot. The trip had it all—nature, beauty, romance, and a little bit of danger, and it was all because I had said yes when John asked me to go to San Francisco for July Fourth and had said yes to Hawaii and didn’t listen to some dumb rules in my head about convention and what you should do.