I was raised within the “just try it” system. At the dinner table, my only requirement when faced with food was to taste it… just a little bite. “Just try it.” And so I would. One piece of lamb. A forkful of beets. A sliver of quiche. My parents allowed that I could be picky if I chose to be — but only after I’d experienced the surfeit of choices firsthand.
I carry that mentality with me to this day, which is the only reason I love olives and live for oxtail ragout. In fact, I’ve found the “just try it” policy so effective, I’ve taken it from the dinner table to the business world and even to the dating front. “Sure,” I’ve told myself over the years, “You’re allowed to date successful, super-smart, tall, gorgeous, wicked-funny men. But you can’t be picky until you’ve at least tried dating other types.” And guess what? The tactic has worked in my favor, leading me to all sorts of self-revelation and a good amount of fun. Here, in order of their appearance in my recent years, are some of the surprising types of men I’ve dated, all of whom I’m glad I did. Each of them taught me more about life and love than I could have imagined.
1. The guy who is attached at the hip to his mother
I wasn’t put off by the fact that he was almost 30 and lived at home until the day he asked me to pick him up for a romantic date that would start at the movies. When I arrived in my Saturday night best, he was sitting in the kitchen talking to his mother. “Have a seat,” he said. “I figured we’ll skip the movie and hang out here with my mom.” A version of this happened no less than eight times in one month with this same guy. She was a nice enough lady, sure, but she seemed to creep up into everything we did, making it hard to get to know him as an individual. The clincher: As we were making out alone (finally) in his basement apartment, he heard his mother’s footsteps upstairs and called out, “Mom, come down here and tell us about the party!” I was still in shock as she settled in with us for the rest of the night. I’m surprised I stuck around as long as I did. I wasn’t used to hanging out with a mom on my dates, obviously. I’m the girl who answers my mother’s questions about my life with one-syllable replies. (“Fine. Good. Fun.”) But after spending so much time with this guy’s mother, I realized: Well, gosh, if I’m going to hang out with a mom, I’d rather it be my own mom.
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Why I’m glad I dated him: As exasperating as his mother’s presence turned out to be, the light in his eyes when he talked to her was heartwarming. Sure, she’s probably doomed to play the role of the monster-in-law to her son’s future wife, but after dating a few bitter sons since then, I learned it’s better to be with a man who loves the most important woman in his life rather than hates her, right? And after dating him for three months, I actually started hangin’ out with my own mom and opening up to her more — and she still has no idea she has this stranger to thank for it.
2. The short, bald, struggling guy
I met my comedian date at – where else? – a comedy show (not his own) through a mutual friend. And though I wasn’t floored by his physical attributes, I was seriously impressed with his confidence. He was a foot shorter than me with a gleaming scalp and an empty show schedule, but that didn’t stop him from cracking lots of ba-dum-pum jokes, telling me I was “so pretty,” and declaring that he’d feel like the luckiest guy in the world if I’d go out to dinner with him. Well, the guy who had just dumped me certainly didn’t feel that way, and it felt good to hear it. He told me later it was his “Fake it ‘til you make it” approach meant to cover up his insecurities around women — but guess what? It worked like a charm on me. It worked so well, in fact, that we casually dated on and off for over a year. I still cherish the nights we spent walking for hours around town, popping into galleries, performance shows and comedy clubs, laughing all the way.
Why I’m glad I dated him: Because an uplifting date is a good date... especially if it’s with someone who doesn’t remind you of your last bad boyfriend. Even though the relationship didn’t develop into a long-term thing, we decided at least it was better to be in feel-good company than miserably home alone. It’s been four years since we last went out on a proper date, but we’re still friends to this day. When either of us needs to smile, we both know who to call.
3. The workaholic
I work long hours, but I don’t work late into the night and every weekend — unlike one man I dated for five months. At first, I admired his work ethic. He stayed at the office until he’d gotten his layouts perfect. He’d come in on Sundays to get a head start on the week. He’d call in on vacations to be sure the work was being done to his standards. In turn, I stayed at the office later myself, got more accomplished, and my work improved. And when we went out, we did it well. Very well. Hundred-dollar dinners of oysters and steak at 2 a.m. were not unusual. As we’d be ushered into a private celebrity event with people he worked with, he’d say, “Now aren’t you glad I took on that extra assignment?” At first, sure, I was happy. It was exciting. But eventually, I found myself going solo to dinner parties at his friends’ apartments, searching for someone to take his ticket to the theater at the last minute, killing time for hours on a Saturday while he ran to the office to deal with “just one quick thing.” I tried hard to work our dating schedule around his demanding job, but in the end, “nagging” him about wanting a bit more of his time got me dumped. (Thank goodness.)
Why I’m glad I dated him: Dating an extreme type like this made me appreciate men who are more even-keeled. I had to re-learn similar lessons when I dated The World Adventurer (who spent too many months away from me spelunking and swimming with sharks) and Mr. Life of the Party (whose overactive social life only rested for about two hours on Sunday afternoons). Through them all, I learned that a person’s time and company is of greater value than his celebrity friends, exciting adventure stories, or even cold, hard cash.
4. The language-challenged foreigner
On my first date out for sushi with an Eastern European man I’d met, he ate the entire mound of spicy wasabi in one bite, then sat quietly with tears in his eyes from the burning sensations in his mouth. “That not the guacamoles,” he finally said. Because I’m a writer, I always assumed I’d be attracted to those who shared my language — much in the way an accountant would probably be more drawn to a saver than a shopaholic or a musician would find it hard to sample new pieces for a tone-deaf date. Still, I couldn’t help being attracted to this oversized man who’d ask me, “Where the bread we get for dinner?” and email me sentences like: “My friend will join with to restorant. She amazing women.” My friends were as confused about my attraction to him as I was about what he was saying, but there was something about him I was drawn to, and I continued to date him until I figured it out. It was this: He had a heart the size of South America, and I wanted to learn from it. He was generous and kind — and more than once, he drove to the airport to pick up friends of mine he’d never met. When I saw how important friends and family were in his life, the language barrier didn’t seem like a very big deal. (In the end, it did turn out to be a big deal, but it wasn’t the only reason for our breakup.)
Why I’m glad I dated him: In the two years we dated, I learned that actions speak louder than words in whatever language you speak. He taught me more about how to be a good, selfless, loving person than any other man I’d known before. After meeting this man, my dating priorities shifted permanently: “has to have a huge heart” has been at the top of the list ever since.
5. The shy accountant
He looked, literally, like a cartoon drawing of an accountant. He had brown horn-rimmed glasses, a gray suit, and a tan trenchcoat. His hair was combed and pasted in a side part like a 1940s newspaper executive would wear. He looked like the “before” version in “before and after” photos. And when I first got “stuck” talking to him at a friend’s party, I didn’t feel much like chatting, so I just asked him lots of questions about himself. He was sweet and, it turned out, very interesting: Before becoming an accountant, he had worked for a company that transported artwork that had been sold or needed cleaning. He told me fascinating stories about going to million-dollar mansions to dismantle and move sculptures the size of my kitchen. In the end, he was more enthralled by the business aspect of the job than the labor (which led to his current career choice), but he had some of his own artwork displayed at home and planned to revisit his craft someday. I mentally slapped my own wrist for judging this quiet man too quickly. Who was I to assume that “quiet” meant “boring,” and that “accountant” meant “uncreative?” I dated him for two months before I admitted the spark just wasn’t there…but it was a fun two months.
Why I’m glad I dated him: I took away two things from the romance with an accountant. First, the obvious: It’s foolish to overlook someone based on the package he or she comes in. And second: Before the accountant, I was convinced that the more I had in common with a man, the better off we’d be; now I believe it’s not how many things you have in common, but rather, which things you share (attitudes, goals and senses of humor top my list) that truly matters. Which is why I’m also glad I dated The War Activist and The Starving Jazz Musician, even though none of those relationships stuck. What’s boring, I’ve learned, isn’t people in gray suits — it’s dating someone from whom you have nothing new to learn.
6. The kid I went to grade school with
When I first knew him, he was a scrawny kid with a bowl haircut who sang “Jailhouse Rock” in our fourth-grade play. A decade later, we spent a young summer dating each other (and never even made it past first base). Two decades later, he was standing in front of me at a movie screening when we both happened to be visiting my hometown. He’d grown up, I’d grown up, and though it seemed odd to imagine dating that little kid from the lunch line, it was clear to me that had I met him some other way (say, in a bookstore), I would have liked him as more than just a friend. So why not test the waters 20 years later, I wondered? We spent our reuniting first date talking about old teachers and our school’s International Day, but he and I really hit it off romantically. In fact, we’ve been dating for awhile, and things appear to be, well, making the grade. I don’t know what will happen for sure, but my spirits are soaring.
Why I’m glad I’m dating him: In my single periods, I always used to wonder... Can recycling relationships actually work? Have I already met the person I’m meant to be with? This man is proof that maybe, just maybe, it can. Not just because we were both open to the odd idea of stepping backwards in our respective lives to find someone we might want to share our futures with, but also because it’s clear that a shared common background makes for a smooth beginning in a relationship. Just like all the other surprising types I’ve dated, I’m glad I decided to “just try” this one out.
Amy Spencer is a freelance writer who has written for Glamour, Real Simple, New York magazine and Maxim, among other publications. For the other side of the story, read6 types of women you must date….