5 Types of Guys I Dated After Divorce (And What I Learned)

Dolce & Gabanna

Dolce & Gabanna

I stopped dating a man because he was too cheap to buy quality cheese.  

Of course, there’s a backstory.

When I’d treated him to dinner, he unabashedly ordered courses of food and expensive wine. Even though I was a single mom supporting myself, I didn’t mind. I figured sharing expenses was the norm as I entered the dating scene. He’d return the favor, wouldn’t he?

Imagine my surprise the very next day when he took us wine tasting then protested over a $6.00 wedge of Jarlsberg. 

“I’d never spend that much money on cheese,” he scoffed. I shared a confused sideways glance with the cheese monger in the grocery store. Oh, God, I thought. We’re over. 

This guy fell into that horrible abyss, The Cheepskate. Once one falls into this category, man or woman, they never come out. It’s just how they’re wired.

I had no way of knowing the cheapskate would be among a revolving door of men who would end-up in cast-off categories including The Artsy Bad Boy, The Geeky Genius, The Too-Nice Guy, and The Me Monster. 

Dating after divorce left me with an impressive daisy chain of mistakes. Manstakes. Oh, but they were often fun and always edifyingly necessary toward finding the one who was just right for me. Here’s a list of men you may encounter on your dating journey (and what you’ll learn if you do.) I believe men and women, equally, fill these categories. Sometimes, we recognize pieces of ourselves in them, too. Dating is about recognizing how certain personality traits meld with our own. Without further ado, a few of the most memorable men I dated.

The Cheepskate  

Cheepskates are out there in droves. 

While it’s very important to be mindful of money, and we’re all on a budget, the cheepskate has no problem spending your money. The benefit of dating him is he’s usually fun and up for anything, anytime. Sky diving? No problem! Want to see Wicked? He’ll be on your doorstep in a flash (as long as you’re paying.) We all need companionship but it’s important to find someone who won’t use you. Too many women are desperate for attention and allow these men to linger. I know I did. After a while, I realized decent men, at the very least, split costs. 

The Artsy Bad Boy

Divorce often renders us completely vulnerable and lacking self-esteem - bad boys pray on this. Does he make a booty call after no call at all? Expect you to drive long distances to see him when he won’t drive to see you? I won’t get into the sordid details of the torrid relationship I had with a man like this who wasted two years of my life. But I will say it was exhilarating. He was an executive in San Francisco, smoldering and well-traveled. He introduced me to a sexy, alluring music scene and sent emails of how beautiful I was and how he’d “never felt this way before.”  (uh-huh) I stupidly believed him while dating veterans would recognize  this “player type” and move on. 

I don’t necessarily regret it.

Bad boys are often stepping stones to reclaiming one’s self-worth. It was only after my self-esteem was obliterated that I realized its value, reclaimed it and held it tightly.  

The Geeky Genius

I dated highly educated men who were professionally accomplished. Intellectually, I enjoyed interesting conversations and the connecting intimacy it afforded. These men often respect women’s opinions and we can imagine growing old with them. The downside? Some I encountered slowly revealed arrogance. Suddenly, I was no longer an equal partner but criticized and/or condescended to. One even instructed me to “take notes” during a conversation. The upside? I learned the importance of finding a partner who had interests, hobbies, intelligence and experiences.

The Too-Nice Guy

After dating a cheepskate and bad boy, a man who was boyish seemed refreshingly safe. Nice guys don’t use women, and in this way, nice guys absolutely win. I dated a man who was perpetually happy which was refreshing after riding some men’s moody rollercoasters. But he was a clinger who wouldn’t let me miss him. Incessant phone calls, text messages and emails flooded my in-baskets.

Too-nice guys often lack self-esteem and need constant reassurance that can feel possessive and suffocating. One such man said he loved me on the third date. It scared the hell out of me. It was in dating the too-nice guy that I realized I was no longer desperate for a man, but rather someone who found himself to be of value. 

The Me Monster 

I learned the most from a me-monster-narcissist who dated me because he thought I was of value to him, like a commodity. Narcissists use people to achieve goals and are often social climbers craving money and adoration. 

While I was of value, he professed his love, whisked me off to Hawaii and flew us privately to Las Vegas (when we weren’t at his home on Lake Tahoe.) I mention these things not because they were necessary to my happiness but because it’s what narcissists do – they try desperately to impress. After a few months, I recognized half-truths and missing details in his stories. Our conversations were about him, his children, his ex-wife, his business dealings, his friends. I was simply inserted into his world. He was bored meeting my parents, dismissive of my friends and increasingly apathetic toward my child. 

This ended abruptly and on his terms, of course. Our entire relationship was on his terms. I later realized if you feel you’re being injected into someone’s life, you probably are. 

Perhaps the Goldie Locks ending to my decades-long dating story is I never lost hope of finding someone who was possessed of positive aspects of each personality type, and especially, someone who was the foiling balance to my own quirks and imperfections. We all know some personalities meld better than others. We’re all imperfectly human. Dating is your opportunity to slowly ferret through different types of people, hone-in on what makes you happiest, recognize dangerous behaviors to avoid and use this knowledge to make wise choices for your future.