Last First Date

by Jennifer L. Hollis

In my early thirties my boyfriend and I broke up at 7:30 in the morning standing calmly in the upstairs hallway of our house. Three weeks later, I moved into a third-floor rental with exposed brick walls, a claw-foot tub, and a roommate. One night, during my nightly performance of Six Cocktails and Six Hours of Cable, a thought occurred to me: I wonder if he’s back to online dating.

I did not hesitate for one second, call a friend, count to three, or think gentle thoughts about my commitment to self-care. A quick search for his age and zip code on a site I knew he had used in the past yielded a long list of matches. And there he was. After making up a fake login, I read his whole profile.

When I sent the link to friends, they clucked sympathetically. Then they asked me to put down my laptop and take some steps to move on. They were right. I stopped stalking his profile, bought a red leather jacket, and wrote my own personals ad.


It is hard to overstate the awkwardness of online dating, at least as it was practiced when I started more than fifteen years ago. Back then, people still thought it was dangerous to go on dates with strangers. We used computers (not phones) to type out long profiles on websites (not apps). When I started online dating in 2002, I was a graduate student at Harvard. It’s possible I passed Mark Zuckerberg in Harvard Yard while he was still an undergraduate.

Today, almost as in olden times, you meet on a screen, exchange some basic facts, and then try to translate this into a conversation over Fair Trade coffee and a blueberry scone. To make matters worse, my life includes divinity school and playing the harp for dying people; a newspaper reporter once called me the “midwife of death.” There’s no such thing as casual conversation once you’ve asked me a few questions. We are either going to talk about religion or death, and it’s a challenge to flirt over either topic.

“People date in their twenties because they love dating,” a friend told me when I complained. “They date in their thirties because they hate dating.”

I went on a lot of first dates. I met a composer who wanted to interview me for a colloquium presentation. I met a Spanish teacher who kissed me on the cheek and told me about his students. I met a sad photographer who stood in my driveway at the end of our date, asking, “What do I do now? Do I kiss you?”

On a first date with a young chef, I mentioned that I was hosting a dinner later in the weekend and didn’t know what to cook. Hours later, I dropped him off at his apartment and he asked me to wait in the car for a minute. He came back with a huge white bin of salmon, romaine, and cucumber juice. “Grill the salmon, char the romaine, and add the cucumber juice to the gin and tonics,” he said. “Your friends will love it.”

I met a couple of people online that I already knew in real life. I corresponded for weeks with a sharp, literary fellow who corrected my grammar and talked about reading piles of midterms. When he sent me a photograph, I gasped. He was on the faculty at the university where I worked. In fact, we were on a committee together, and he had stopped by my office earlier that day. Grateful I had never sent a photograph or told him my full name, I quickly ended our correspondence and never told him that it was me.

There were plenty of dates I should have known better than to go on. One man’s photo was a selfie of his bare chest, taken in the bathroom mirror. Although this struck me as cheesy and vain, I agreed to meet him. He wore great cologne and reminded me of an older boy I had a crush on growing up. While we drank fancy drinks with fresh herbs and lemon slices, he mentioned that he had written a novel, and I asked if he was trying to publish it.

“No, it was published two years ago,” he said. I congratulated him, and he looked genuinely confused. “Information about my book is all over my website,” he said. “You didn’t Google me?”

“I don’t know your last name,” I said. He handed me his business card.

Later that night, I read a book review that mentioned his hometown and high school graduation year and realized he was significantly older than he had reported.

He emailed a few days later. “How did I do?” he asked.

“You were doing fine until I searched for your website,” I wrote back. “I’m not sure how the age on your profile and your high school graduation year could both be true. Were you a boy genius?”

We did not go out again.


The grief of my breakup lingered. I no longer trusted my own judgment about relationships. How did I get to be thirty-four, childless, and living with a roommate, like a college freshman? I was stumped. I wanted to get married, but I was devoted to my independence. I liked my apartment, but secretly feared that I would choke on my popcorn-and-wine dinner and lie dead on the Craigslist couch until my roommate came home from work.

And I was furious at the process of building a new relationship all over again from scratch. I felt like a marathon runner who had gone to mile twenty-five and was then forced to return to the starting line. The optimism of my twenties was gone. I was worn out from devoting years of my life to relationships that ended, sometimes with a whimper, more often with a bang. I was sick of having, as a friend once said, “another fucking growth experience.”

I needed help. I wanted a Dating Committee to review my stories and approve key decisions. I called on my friend Anne, a high-school Spanish teacher known for her strong opinions and, as she likes to say, dangerous honesty. When I mentioned a man who lived twenty miles away, she asked, “Do you want to spend three nights a week in the suburbs?” She was disgusted when I considered going out with someone who told me he “spoke cat.” After three dates with a hilarious vegetarian I did not want to kiss, she explained that this man was a new friend, but not a boyfriend.

Although he did not know it at the time, my brother Adam was another charter member of my Dating Committee. When I told him that I didn’t know how interested someone was, he only had one question: “Is he calling you to ask you to do things? That means he likes you.”

When I worried that an ex was getting back in touch to tell me that he was dating someone else, he laughed. “No man is ever going to call you to tell you he’s dating someone else. Those guys just drop below the radar. This guy is sniffing around to see if you’ll take him back.” I told Adam about a handsome date who wore a terrible purple-checkered sweater. “Just so you know, that was his best outfit. He wore that sweater because he thinks it looks great.”

I loved having a Dating Committee, and I winnowed down and tried to follow their most helpful advice. First dates were only ninety minutes and on a weeknight. I tried to do things on dates that I wanted to do anyway, like trying new bars, restaurants, and cafés. For the most part, I limited this to eating establishments, but early on I convinced someone to meet me at a thirty-minute oil change garage and then go shopping for Halloween costumes.

When the first date didn’t leave me eager to see them again, I said no to a second date. Married friends thought I was ruthless, but I didn’t listen to married people. They didn’t know what it was like. When I met someone I liked, I waited for the fifth date before I let myself get emotionally invested. The reason for this is painful: people disappear. I was ghosted again and again. One day you make out on a park bench and hold hands all the way to the subway, and the next day you never hear from him again.

Finally, I tried not to let dating taking take over my entire life. Years before I started Internet dating or—let’s be honest—used the Internet at all, I spent an entire evening at a bar complaining to my friend Gary about a man who had stopped calling.

Gary listened carefully, and after a while he ordered me another beer. “Captain,” he said, “the only thing we know here is that we don’t know why he’s not calling. There’s only one thing for you to do. Keep on living your big life.”


When it became clear that I was not meeting my husband on my own, my mother suggested that I sign up for a popular dating service. She sent me links to their special offers. She offered to complete the questionnaire and pay for it. I refused to listen. I had a master of divinity degree. I had built a harp from a kit, driven across the country alone in a car I couldn’t entirely vouch for, signed two leases without seeing the apartments, and owned almost no grown-up furniture. I was not going to let this website’s marketing budget convince me that I was their demographic.

But after a man I particularly liked disappeared, I weakened. Maybe this site was where everybody went when they really wanted to get married. Maybe people who were willing to pay a monthly fee the size of a gym membership were more committed to finding love. Maybe I was just like those women in the ads, and two years later I’d be shopping for a wedding dress and saying, “I knew he was the one the first time he took me salsa dancing!” It didn’t seem likely, but it couldn’t be any weirder than the dates I was already going on. I signed up.

Men from this site wanted to have dinner rather than coffee or a drink. They often insisted on picking up the check. For a few months, I ate a lot of free-range chicken with young lawyers. I went out with a handsome scientist whose questions all seemed to come back to starting a family. He wanted to know how old I was, saying he was fifty but still wanted children. Since the last man I’d gone on five dates with was twenty-seven, I had clearly crossed over some sort of demographic threshold. Walking home, I wondered if I was older than I thought I was.

That, as it turned out, was my last first date. I had met my husband a few weeks earlier. His profile was self-deprecating and clever. He quoted Inigo Montoya. He took issue with the word “passion” in the question, “Name five things you are passionate about.” He mentioned that his daughter had helped him answer some of the personality questions.

Our first date was on a muggy September night, too warm for the green sweater I’d insisted on wearing so that he would notice my eyes. Several blocks away from the restaurant, I saw a man on the sidewalk with his back to me and thought, involuntarily, Oh, that’s him. I could date him. My critical brain kicked in and corrected me: I was too far away from the restaurant, and I could not possibly recognize the back of his head.

I walked past without speaking to him. Half a block later, I heard, “Hi, Jen.”

“Sorry to sneak up on you,” he said when I turned around. “I just didn’t want to follow you the rest of the way to the restaurant like a stalker.”

He was warm and talkative, but not overly familiar. I rushed through the quick version of my work in end-of-life care, and he stopped me. “Slow down. There’s plenty of time. I’d like to hear about this.” At the end of our meal, he said, “Let me pay for it. I think people should be indulgent with one another, and I hate splitting checks. You can indulge me another time.”

As we walked around the neighborhood after dinner, he made a little speech. “I just want you to know that I’m not looking for anything serious,” he said. “I just want to date casually, lots of different people. Like I was in high school. Do you know what I mean?”

“Sure,” I replied. I was impressed that he knew what he wanted, but it was none of my business. He was going to have to ask me out four more times before I needed to know what he meant by high-school dating, a term I knew Anne would love. I drove home, assuming I would never hear from him again.

That night, I dreamt I was sitting on a bus, chatting with the woman next to me, when I realized it was the mother of the guy I had just gone on a date with. We arrived at a hotel and sat down on a big cushioned couch.

Then, in the dream, she turned to me and said, “Well, do you want to marry him? Are you going to marry him?”

I quickly collected my thoughts. “I don’t know,” I said. “We just went on our first date, and it ended forty minutes ago.” I woke up and wrote down the dream in case it would turn out to mean anything.


My mother was right. George and I had signed up for that online dating service within weeks of each other. A handful of dates in, we stopped seeing other people. When we got married, eight years ago, I became a wife and stepmother. We bought a house, had a baby, put a koi pond in the backyard.

My brother Adam gave a toast at our rehearsal dinner. He joked about the men I had dated over the years. Because he is a very good brother, he declared that most of them were not good enough for me. He talked about watching me try to balance my need for independence with the desire for love and partnership, and his feeling that most of the men I dated didn’t get this about me.

“Then Jen started dating George,” he said. “And one day, she came over to my house wearing a T-shirt with the words ‘One Man Wolfpack.’ She told me George had given it to her for her birthday. That’s when I knew she had met the right guy. I knew that anyone who would give a new girlfriend a “One Man Wolfpack” T-shirt was the kind of person who understood my sister’s need for independence,” he said. “And I liked that he wasn’t afraid to make fun of her for it.”

Marriage is a strange container, full of comfort and constraint. I don’t want to leave it, but I don’t rest easy in it either. A few weeks ago my husband and I started joking about people we might leave each other for. I rattled off some ideas and he offered suggestions and approval. Then I asked for his list.

With the shocking honesty that I’ve learned is a feature of most marriages, he said, “Oh, I wouldn’t leave you for another woman. But I might leave you for a boat.” A few weeks later he signed up for a sailing class. We have both agreed that this is just a coincidence.

Published on October 17, 2019