Intro: 108 First Dates — and one perfect lover

Feb. 1, 2022: Today is my anniversary. The day that I promised to love my husband forever in 1995.

I do love my husband. I always will. But on Thanksgiving 2005, I knew I couldn’t stay married to him. For the next decade, I struggled long and hard with a single burning question: Why Divorce?

What happened that night is not as important as the fact that, for the first time in our marriage, I saw with pained eyes that we loved differently, played differently, and looked at the world through very different lenses. Rather than our unique perspectives bringing us closer, it became increasingly clear that we were living separate lives. Had our two kids, two freelance careers, and a five-bedroom house in the suburbs snuffed out the passion that once bonded us? If so, could I live without the true love I longed for — for the rest of my life?

Sure I could. On the surface, and even a few feet beneath, things were fine. My husband and I worked in related creative fields enabling us to collaborate well in and on our businesses; we parented alike, laughed often, and by and large made our upper-middle-class life work.

Here’s the rub: I wasn’t happy. Yes, he supported me in all of my professional decisions, but he’d never go with me to events or participate in the business I was building. And I really wanted him to. Year after year, I kept trying to make things better — for him, for me. As time passed, however, I felt my heart dying a slow, sad death. There wasn’t enough wine to make that emptiness ebb, and eventually, my sorrow turned to anger. I knew my soul wouldn’t put up with this for much longer. It was pissed and knew things had to change. I had to change them.

The summer I turned 50, that inner knowing crystallized.

My family was spending the week by the sea at Bethany Beach, DE, and on the morning of my birthday, I woke up with a symphonic thought screaming through my mind. It was a line from Kerry Russell’s film, Waitress; the part at the end when she held her newborn daughter for the first time — a child she didn’t think she wanted — and uttered, “We’re going to have so much fun, little girl!” I knew that would be true for that inner child and me of mine.

A month later, we took our daughter Anna to VCU in Richmond, VA, to start her freshman year. As we drove into town, it was as if a magnet were pulling me toward my future. I felt like I’d lived there before.

For the next year, I regularly traveled from our suburban home in Northern Virginia to visit her, staying downtown at the Omni Hotel in a room that smelled like orchids. I repeatedly requested the one that overlooked the river, and as I stared endlessly out the window, I imagined my life there.

The day we moved Anna into a 1900s brownstone in the Fan district of town for her sophomore year, I knew I wanted — no, needed — to live in a place like this and returned a week later to take her to lunch. As we drove down the business district in town, an Office For Rent sign caught my eye. Sitting in the booth of our favorite sushi place, I rang the realtor and toured the place after I dropped her off. Three nice-sized rooms, a working fireplace, brick walls, and a view of the street — it was perfect. By 7 pm, I agreed to sign a three-year lease.

Then I called a residential realtor I’d befriended a few weeks earlier, asking if she knew of a house for me to rent. “Nope, that’s a waste of money,” Jenny insisted. “Buy a house. It’s affordable in the Fan district of Richmond and a great investment.” When she showed me the 1200-square-foot carriage house built in 1911 just a few blocks from the office, I knew she was right.

On November 1, 2014, I moved into that office and my new house, and every time I turned the key to open those doors, I did a happy dance.

As whimsical and spontaneous as my story sounds, I promise you this was not a simple step to take.

Our son, Dylan, was a sophomore in high school then, and my husband was not eager to face the reality of the situation — much less make any changes himself.

I spent the next year weekly traveling I-95 between Arlington and Richmond, checking in on Dylan while trying to plant myself in a new town, manage and maintain my clients and the growth of my PR firm, and grow the video and internship portion of my business.

Every time I drove back to Richmond, I felt my spirit lift off. I parked my car outside my house and rode my pink bike around town like a tourist discovering the new place I’d chosen to call home. I also explored what I liked to do, play with, and eat. I know it sounds silly, but after 20 years of cooking to the tastes of my kids and husband, I honestly forgot what my favorite foods were. I began to practice filling the kitchen only with things that tasted good in my mouth (mushroom soup, chickpeas and croutons on iceberg lettuce, and rice cakes with marmalade jam). Ditto for the colors I painted the walls (purple and yellow), the furniture I bought (black and white), and the covers on the beds (red). Within months, I was living in a house of my making; it was filled with candles, crystals, and sculptures of Siddhartha. It was all me, all mine. I could hear my soul clapping.

Frankly, it was as exhausting as it was exhilarating. The winter of 2015 was the coldest the east coast had seen in years, and when the temperature hit 2 degrees, I came down with the worst flu I’d had in my adult life. Despite being wrapped in my ruby-red blanket and embraced by the sunshine beaming through antique windowpanes, my life seemed frozen and hopeless.

Then my fever broke. And Spring came.

One day in April, when my husband was again refusing to talk to me about our situation, I decided it was time to begin exploring my romantic future. I put my profile on J-Date.

My logic went like this: I had married a very lovely, kind, and gentle Catholic man, but being a nice Jewish girl from Philadelphia who lived in Israel and loved her heritage, I wondered if maybe I should have considered meeting more nice Jewish boys during the dating days of my 20s.

I also made a vow to myself — advice I’d given a dear friend whom I had helped through her divorce years before — that I’d go on 100 first dates. She hadn’t dated before marrying, and it struck me that she needed to meet at least 100 men before knowing herself at this point in her life and finding what she wanted and needed in a partner. I figured if that approach could help her, it would benefit me, too.

For the next year, I dated 108 men.

Really. I did.

For those who think this sounds like a terrible thing to do, I assure you that my approach to finding true love wasn’t as premeditated as it sounds. I was straight-up curious about how men think. What do they want from their lives, loves, and lovers? What broke up their marriages? Why didn’t some of them ever marry or have kids? What made them choose the careers they did? What was their childhood like? Did they enjoy their lives? What did they really want from, and for, themselves?

I also was curious about their dating experiences. How did they feel about the women they’d met through online dating sites? How did those relationships play out? And did they think the dating process was wacky, wonderful, or awful?

I had so many questions and so much to learn, and found that on those first days, the men were happy to share. They wanted to talk about what mattered most to them and seemed willing to take down the walls that might have surrounded them in other areas of their lives.

If that’s not reason enough, attribute my year of serial dating to being an occupational hazard. A journalist for more than three decades, I am trained to do ridiculous amounts of research for any story I’m writing. I also tend to shift into interview mode when I am exceptionally curious, anxious, or bored. (That training came in handy on a variety of dates — where we clearly hadn’t filtered each other properly — and I wondered how long it would take me to drink this glass of Pinot Grigio before gracefully getting up to go. I’d just ask more questions about my date until it seemed polite to leave.)

Indeed, being polite and respectful was high on my priority list.

And no, not all of my dates were in person. As per online dating etiquette, it all started as email exchanges — first on J-Date, but when I discovered I indeed did not really want to be with a man just because he was Jewish, I signed up for Match.com.

My ego is pleased to report that I got hundreds of pings over the course of that year, and for that, I thank my photographer friend John David Coppola for taking a really nice photo of me on a very good hair day. I also give thanks to a man I met early in my online dating experience who advised me not to respond to an inquiry if I wasn’t interested. “If you don’t say anything, we take the hint,” he confided. “It’s easier on us that way.”

Heeding his advice, I adopted the traditional online dating checklist:

At a glance: I took a “blink” approach, weeding out potential suitors whose pictures or bio didn’t appeal to me as not being a good fit.
Email conversations came next for those who did catch my eye: From here, I filtered based on their writing. I communicated only once or twice with those who sent me single-word responses, couldn’t spell or craft a sentence at all, or were downright rude (yes, there were more than a few of those).
Step three was a phone date. If we mutually felt any sort of spark, we arranged to chat on the phone. This was another teachable moment for me, for I realized how much someone’s voice played into my impression. I always appreciated it if they made me laugh. If I liked how they sounded and what they said, and they felt the same, we arranged to meet in person.
When the big moment arrived: I went in being open-minded, curious, and respectful — even when, during the first date, I knew this wasn’t the magical one I was searching for. Every man had something interesting to say; I appreciated their frankness and their willingness to share their stories.
Regarding who pays: Often, but not always, when food or drinks were involved, I paid for myself. It wasn’t a hard and fast rule, as I think it’s gentlemanly to pay for a lady. But I also didn’t want anyone to think I was taking advantage of the kindness they were showing me, I assessed the money issue on a case-by-case basis.

What did I learn on my 108 first dates?

I found that I was meeting five types of guys:

The narcissist: Despite the fact that I appreciated and learned from each and every date, there was a remarkable percentage of men that I met who slipped into speed talking. If you’ve been on a date recently, you’ll likely have had this icky sticky experience — whether you are male or female. It seemed that they were incredibly fixated on sharing every detail of their lives, assumedly to impress or perhaps because they were nervous, they didn’t take as much as a breath to have what I consider to be a conversation. Although I am eternally curious, this one-sided experience left me wanting to shower and nap. There were also those who seemed to have no sense of what it means to kindly court a woman. A case in point was the man who, as we left the restaurant, bought flowers — for his mother. I was often able to filter this type of gent on the phone, but a few slipped through the cracks, making me question the whole process.

The hedonist: Yes, of course, the point of finding true love is also to find a lover. But on that first date, a man inviting me to have sex — and in several cases oral sex — is just a turn-off. There was also often some sort of touching involved on these types of dates, and that made me feel really uncomfortable. Granted, this approach might work for some. But subtlety rules in my world. Call me old-fashioned, but I get wigged out when talk of sex happens within the first 15 minutes of meeting a man. After all, if he’s going to jump the gun on date number one, what’s gonna happen if we get into bed together? The more dates I had like this, the clearer it became that I was looking for a true gentleman, someone who instinctively knew when I was ready for him to make that first move. I began to wonder if any man would be tuned into that frequency. In addition to giving me the chilly willies, meeting a slew of hedonists just plain made me sad.

The high school heartbreaker: This type of guy was the one that I truly appreciated, for it catapulted me right back to high school when the object of my affection didn’t return my feelings. I don’t think anyone who has been on a date hasn’t been lashed with that cold flash of rejection. It’s amazing how long you can be away from that high school experience — but that same feeling still stabs you in the gut. I met two men that I experienced this early on in my dating experience, and I truly am grateful for them. Working my way through those feelings, and finding a way at 53 to laugh at the reality, was incredibly important.

The friend: Sadly, I met a few handfuls of men who were truly lovely and wonderful and wanted to have a relationship with me — but I didn’t feel the same. Clearly, the feeling of heartbreak, or at least heartache, goes both ways. I do hope to keep some of those men as friends for a long time to come, but understand that’s not possible. This game of finding true love is so tough.

My true love: Finding this man is the goal, right? It’s the challenge, the pinnacle, the magic, and the reason that we are on this online dating quest. As I worked my way through all those dates, I kept asking: Where are you? Do you exist? Am I crazy to think I’ll ever find true love again? Will I be alone for the rest of my life? By date 100, I started thinking I just needed to pick someone to sleep with so I could get over this hump.

On date 108, I met my match.

I found his profile on April 5, 2016 and reached out to him in a short email that said, “Oh, I think we’d really like each other.” In all of my experiences, I rarely wrote first; but there was something about his bio that was so much like my own; I felt I knew him.

After only a few emails — one where he asked me to respond to five questions that were so clever and interesting I was immediately smitten — I had to hear his voice. Although talking on the phone is not his favorite way to communicate, as I discovered later, that first chat was absolutely lovely: super nice, super smart, funny, clever, and he had a sweet voice. I totally wanted to meet him.

We went on our first date on April 19. That afternoon, I’d flown into DC from a weeklong business meeting in Kansas City, changed quickly, and walked out of the Marriott Hotel to meet him as he was crossing the street. He looked just like his photo (a relief, as that wasn’t always the case) and smiled a crooked grin as he looked at me over his glasses. What was he thinking?

I didn’t care. By now, I had been on so many first dates that I’d become an expert at distancing myself from the outcome. He looked as cute and kind as he sounded on the phone, and I was determined to have a nice evening.

We choose to sit at the bar in a French bistro across from the hotel. He picked three appetizers we might like from the happy hour menu and asked me to pick the one I wanted; when I chose the chicken quesadillas, he said that was his first choice. We drank a little wine and talked and laughed, and when we were finished, he asked if I’d like to go somewhere else for another drink.

This was a first. In addition to being slightly wonky and very witty, he was tall, thin, and handsome (totally my type). But what got me was that he was a gentleman who wanted to stay and play. I thought about this as we sauntered to a hip spot near GW University, where we shared fancy cocktails with giant ice cubes and talked for two more hours. The details of our chat didn’t stick as much as the feeling that this man was the most interesting person I’d met since I met my husband in 1991. His sparkly eyes reminded me of George Harrison, and I just wanted to keep listening to what he was telling me about his career and his love for his three kids.

On the way back to my hotel, he held my hand and said aloud how soft it was. I went to hug him, and the moment I touched his chest, it was as if the sky opened up, for my immediate thought was, “Holy moly, there you are!”

I was so happy and excited that I was very close to ignoring my no-fooling-around-on-the-first-date rule. The next day as I awoke from a nap on the train back to Richmond, he had texted me saying that if he was on the train, he’d probably be asleep. And, he said, how nice it was to meet me, that he couldn’t stop smiling all day. Me, too!

For the next three months, I discovered a part of me that had been asleep for so long. We didn’t do much of anything standing up, but when we did it was playful and sweet (mini golf and a winery), and there was something about our banter that made me want more, more, more.

It wasn’t until our third date, when we were lying in bed, that I finally asked, “So I know you are an engineer, but what exactly do you do for a living?” He gave me a few clues that led me to understand, “You are a race car driver?”

Turns out he married his mental acumen and his physical prowess to create a career that worked for him. We laughed a long time about that, realizing that it didn’t matter what we did. There was an attraction and attachment that went as deep as anything I’d dreamed of. When I told him that he was my perfect lover, he simply said, “No, it’s you. You are the perfect lover.”

I sighed, for I suddenly struck me that having him reflect me back through his heart and eyes was exactly what I’d been looking for. My quest was not just to find someone who would be my match — but to find who I wanted to be in this next phase of my life.

I began re-asking myself the fundamental questions I’d asked my dates: What do I want from my life, my love? What do I really want from, and for, myself? This man had given me the gift I’d been searching for.

What became of the race car driver and this writer? That’s a story for another day.

What I will share are a few observations that might make your trip down the dating lane go a bit smoother.

Gentlemen: Take a second look at your profile pics from a lady’s point of view. Many of us aren’t keen to see you sitting in your car, catching a fish, or without your shirt (even if you are an Adonis). Leave us something to fantasize about. Show us your eyes. We also don’t really want to see you with other women (although they seem to you like sweet pics, photos with your teenage daughters actually look like you are dating minors; not really a turn-on).

Ladies: Courtesy counts. I was saddened to hear that many men felt taken advantage of by women who drove up a dinner bill ordering the most expensive things on the menu or had little respect for their date’s feelings. Not nice! I think it might be good to treat them as you’d like them to treat you. If we all attempt to do this, it might make this dating game a little easier.

Take your time with your bio: These 250-word profiles are like truth serum. Even though they may be written on the fly, they speak volumes. If someone says they are religious, believe them. If they say, they are conservative, true too. So if you aren’t — don’t respond unless you are looking to argue or shift your belief system.

Open your heart. Many people playing the dating game are vulnerable. They’ve been in a relationship that ended — and that sucks, even when parting is the best thing for all concerned. Be sensitive and respectful about that. Don’t take advantage. The effort will be returned to you in remarkable ways.

Tell the truth. If you are just in this dating game for sex, don’t pretend you are the marrying kind. There are plenty of women who just want to fool around, too. Clarity is key. But you have to know your motivation; it’ll help you find what you are looking for.