I must have missed Dating 101 in college or was sick the day they taught Courtship in high school. I've racked up a few boyfriends and a...
I must have missed Dating 101 in college or was sick the day they taught Courtship in high school. I’ve racked up a few boyfriends and a million crushes, but while I’ve been successful at most everything else, I’ve been unlucky in love. I was nearing 30 and still dateless and unmarried.
It was a gray weekend in May, with 16 weeks until my 30th birthday, when I reached a sink-or-swim moment. I chose to swim. Actually, I chose to dive in, feet first, without a lifeguard, swimsuit or floatation device.
I decided to go on 30 dates before my 30th birthday. It was a rash decision — I haven’t been on 30 dates in my whole life, let alone in 16 weeks. But with a little help from my friends and some of the most decent men around Puget Sound, I would achieve my goal. Actually, I would go on 37 dates before my 30th birthday. (I’ve always been an overachiever.)
Here’s some of what I learned:
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My first date — the first of 15 blind dates — was on a sunny Tuesday afternoon. I met him at Café Ladro downtown . He was a well-dressed Taiwanese man ready to get to know me. Then we ran into his cousin who had just flown into town after a few years overseas. We spent most of our time talking with his cousin instead of each other.
Lesson: One date is (usually) not enough. My friend Nathaniel gave his future wife a bloody nose on their first date. There’s more to discover about a person than a first date reveals. I went out with Date 1 a week later and we had a great time.
I met him at Madam K’s, a former brothel turned pizza place in Ballard. My college friend Amy set me up with him. We had similar values, so the conversation was easy — until the awkward ending. Did he have fun? Does he know where I stand? Should we shake hands, hug or kiss? Should we schedule another date? Who should initiate it? He walked me to my car and for the next 10 minutes, we barely spoke. When we did, we repeated things we already knew and spoke in half sentences that neither of us understood.
Lesson: Know how you want to make your exit and do it with clarity and class.
Dates 4 and 5
Friday, May 19, will go down in my history as the first time I went out with two guys on the same day.
I met Date 4 at Pike Place Market. We had lunch at Matt’s in the Market, a cozy hole-in-the-wall with great food and an even better view. He was a Patrick Dempsey look-alike, 36, dark hair, hazel eyes, an Italian lawyer. The conservation flowed. This is someone I could hang out with, I thought. I told him about my rule: My dates had to be the ones to initiate a second date.
I didn’t hear from him again.
Lesson: Let a date be a date — enjoy it and let it go. My grandma always tells me to, “Collect, collect and then select.” Relationships are about quality, dating is about quantity.
Date 5 was a 39-year-old writer who thinks deeply and isn’t afraid to talk about his innermost thoughts. We shared our thoughts, and that was about it.
He was a campaign worker who made great conversation and cracked a lot of jokes. The friend that set me up said, “He just graduated with his master’s from Yale and girls fall all over him. Very cute and sincere.” I was confused at first glance because he has a Bill Gates-like build, a bit gangly, glasses. Not five minutes into the date, I saw exactly what she was talking about.
Lesson: While I’m a fan of a hot, eligible man, charming is better than sexy. Yes, it’s who you are inside that matters most.
I drove to Tacoma to meet Date 7, the dentist. He’s 6 feet 5 inches, a good 15 inches taller than me, so that made our greeting (a hug) a little awkward. After dinner, some dancing and some serious sparks, he asked me out on another date. Then he followed up with a voicemail to make plans. I returned his call twice and got no response. Four weeks later, I heard from him again apologizing saying that he’s not ready to date.
Lesson: I was starting to get discouraged. I was getting very little repeat attention from these men. Then I had a revelation: It’s not always about me! Some of my dates had serious issues and I was better off without them.
He was a house painter who took me out on his motorcycle — and the sparks flew. Our physical attraction led to dates 10, 13, 14 and 19. We flirted, we teased, we hung out because being together was better than being alone. Then we realized the truth: Our attraction was skin deep.
Lesson: Any company is not better than good company.
He was the youngest of my dates. A power dater who knew more about urban planning than anyone I’ve ever known. Were we different! Me, a Christian. Him, an atheist. I’m a suburban chick who drives an SUV. He’s a city boy with no car at all.
Despite our differences, we had a blast together and went on three more dates, each meticulously planned. He bought tickets before I arrived, he knew the history of the zoo we visited, and he knew exactly which restaurants were nearby. I learned a ton from him about good men and myself.
Lesson: Planning a good date pays off. His attention to details put his date at ease.
He was a youth pastor from Skyway that my family set me up with. He took me to Red Robin and then we enjoyed a walk along the waterfront. I got a severe stomach ache and I had to excuse myself multiple times to use the restroom. Oh, the humiliation!
Lesson: Embarrassing things will happen. You will feel sick, nervous, uncomfortable or awkward. You will say and do stupid things. On other occasions, I called my date (sorry again, 5 and 31) by the wrong name. Find a way to adapt and overcome — bring your humor (or Pepto Bismol) with you.
He was a doctor from Tacoma who also became Dates 26, 27, 28, 33 and 34. He was attentive, he was kind, he was cuddly. He brought up trips we could take. He mentioned marriage. I was swept off my feet. My friend was like, “Oh, Donna, you’re in trouble.” Then, nearly as suddenly as it started, it ended. The e-mails got shorter, the phone calls stopped.
Ouch! I had fallen the hardest for this guy.
Lesson: Never underestimate the power of inflated expectations. If there were a land called Irrationally Giddy, I could be its queen. Try to stick to what you know, not what you assume. You’ll save yourself a lot of heartache.
On July 31 I hit some balls at the golfing range with a loan officer. There was a spark, but the date was remarkable in another way: I’d reached my goal. Just short of my 30th birthday I’d gone on 30 dates.
So what did I do? I kept on dating. I had found there are plenty of quality fish in the sea and I needed to keep fishing (another lesson learned).
I went on one more date with Date 30 and four dates with Date 31, a schoolteacher. I’m continuing to see both (and another one).
I didn’t end up like Andi Anderson in “How to Lose a Guy in 10 Days,” or find love like Bridget and her diary. That was never the main point. I reaped the rewards of courage, openness and a little bit of madness.
Dating is part of life’s classroom, and the subject I learned most about was me.
Donna Amoranto is a corporate project manager: email@example.com.