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6 Surprising Guys You Should Date

I wrote this story for’s Happen magazine, and I had a blast doing it. First, because it’s fun to revisit the people we dated in our pasts. But also because it reminded me how each person we date teaches us a thing or two about ourselves and about love. I’m not suggesting that these are the only six types of people you should date, or that you should even stop at six. (I’m sure your dating roster has its own unique additions.) But I do suggest that you look at who you have dated and really think for a minute about what you’ve learned from each one.

I really do believe that every single person we date—yes, even the one with the body odor—teaches us something new about what we want—or what we definitely don’t. After all, without learning what kind of people are wrong for us, how will we ever find our way along the path to Mr. Right?

I recently got an email about this story, asking, “So? Did you find Mr. Right after all those dates?” So, what the heck. I figured I’d post the story for you, and then give you an update on the ending.

6 Guys You’ve Got to Date

by Amy Spencer, for’s Happen magazine

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 ragu. In fact, I’ve found the try-it policy so effective, I’ve taken it from the dinner table to the business world 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.


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. 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 buttoning up my top 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 hangin’ out with a mom. I’m the girl who answers my mother’s questions about my life with one-syllable sentences. (“Fine. Good. Fun.”) But after spending so much time with his mother, I realized, well gosh, if I’m going to hang out with a mom, I’d rather it be my own mom.

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, 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.


I met him 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. 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 dated, but we’re still friends to this day. When either of us needs to smile, we both know who to call.


I work long hours, but I don’t work into the night and every weekend — like one man I dated for five months did. 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, got more accomplished, and my work improved. And when we went out, we did it well. Very well. Hundred-dollar bottles of wine and oysters and steak at 2 a.m. 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. 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 worked hard to work around his work, 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 made me appreciate men who are more even-keeled. I had to re-learn similar lessons when I dated The World Adventurer (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 cold hard cash.


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 — the way an accountant would probably be more drawn to a saver than a shopaholic, and 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, “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 drove to the airport to pick up friends of mine he’d never met. When I saw through his life how important friends and family were, 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, whatever language you speak. He taught me more about how to be a good, selfless, loving person than any other man I’d known. After him, my dating priorities shifted permanently: “Has to have a huge heart” has been at the top of the list ever since.


He looked, literally, like a cartoon accountant. He had brown horn-rim glasses, a gray suit, and a tan trench coat. His hair was combed and pasted in a side part like a 1940s newspaperman. He looked like the before 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 lots of questions about him. He was sweet and, it turned out, very interesting: Before he worked as an accountant, he worked in 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, 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 so 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 accountant. First, the obvious: It’s foolish to overlook someone based on the package he or she comes in. 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 which things you share (attitudes, goals and senses of humor top my list). 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 learn nothing new.


When I first knew him, he was a scrawny kid with a bowl haircut who sang Jailhouse Rock in the fourth-grade play. A decade later, we spent a young summer dating (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 bar or a bookstore), I would have liked him. So why not test the waters 20 years later? We spent our reunited date talking about old teachers and our school’s International Day. But Grade School Guy and I really hit it off. In fact, we’ve been dating for four months, and things appear to be, well, making the grade. I don’t know what will happen for sure, but my spirit and hopes 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 work. Not just because we were both open to the odd idea of stepping backward in our 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 relationship beginning. Just like all the other surprising types I’ve date, 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.

Since I wrote this story…

Things worked out so well with “the kid I went to grade-school with”…I married him. And I really do thank, in my heart, all the surprising guys that led me there—the good, the bad, the rude, the weird, the ones that really liked me and the ones that really didn’t. Without them, I might not appreciate what an amazing match I got in the man I married. Sheesh, though, talk about a “surprising” date: I had no idea it would be my very last one!

If you’d like, you can read this story on, including some reader comments debating number one on the list.