Introduction Part 1: 108 First Dates — and one perfect lover

An Introduction to Why Divorce: 5 Reasons to Leave
I love my husband. I always will. But on Thanksgiving 2005, I knew I couldn’t stay married to him. We’d wed 10 years earlier, and 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 just 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, my inner knowing crystallized.
My family was spending the week by the sea at Bethany Beach, DE, and 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 me, and that inner child 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 traveled regularly 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 view of the street — it was perfect. By 7pm, 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 at the time, 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 travelling 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 set out to explore 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 a practice of filling the kitchen only with things that tasted good in my mouth (mushroom soup, chick peas and croutons on iceberg lettuce, rice cakes with marmalade jam). Ditto for the colors I painted the walls (purple and yellow), furniture I bought (black and white), and 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 of mine who 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 at least meet 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 100 men.
It turned out to be 108, actually. Yes. 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, 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 willingly to take down the walls that they 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 of 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, 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 caught my eye: From here, I filtered based on their writing. I communicated only once or twice with 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 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 were 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. 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 a 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 make 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 with 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.
What happened? Listen to the next podcast to find out!
And remember: If you’d like to share your story or be interviewed, send me an email for consideration at hope@hopegibbs.com and check out our website: www.WhyDivorce.us.