What I Learned From Dating 12 Men in 6 Months


woman riding horse

Once I knew divorce was in my future, I began thinking about dating, something I had not done in 15 years. The idea was both frightening and exciting, and part of my thought process was, “with whom?” After some thought, I told my co-worker Lance I was getting divorced, and he responded by asking me out for drinks. Perfect! I agreed, then tossed in the stipulation that I wanted to wait until my divorce was final.

We flirted for the next six months of my separation, during which time I concocted a plan to let him take me out on a few dates – just for practice, since it had been so long since my last first date. But I made the mistake of telling him it would just be practice. The next thing I knew, he was dating someone else and I needed a new plan.

What followed was a string of dates best classified as a learning experience.

Date #1: Jordan the Executive Recruiter

Jordan was a man I met online who I recognized from my court-mandated parenting class. Our date went well enough – I was starting to remember how flirting worked – when he surprised me in the parking lot with a kiss I was not ready for and which I dodged spectacularly.

In the following days, he made it clear that he wanted to continue to see me and I realized his strategy would be to woo me with his money. He invited me to accompany him to a business meeting in San Francisco (about as far from my home as I could get without leaving the country) where I could shop, visit the spa, and play tourist before returning to the Ritz to dine (and stay) with him. While the offer was generous, it was a date rape waiting to happen, or at least an invitation to being a kept woman.

I cancelled our upcoming second date.

Lesson Learned: Money can’t buy my love.

Date #2: Dave the Teenage Girl

I met Dave on my first kid-free weekend post-divorce when my girlfriend dragged me to this divey bar. I was not impressed, but when our paths crossed again online, I figured I’d give him a shot. If nothing else, it’d replace the icky feeling I had from my previous date.

We met for drinks and it went better than expected. We went out again a few days later, then a few days after that. Over the next few weeks, Dave and I spent lots of time together, mostly at his house where I made dinner and played with his darling children while trying to get Dave to keep his hands to himself. He seemed convinced I was what he needed, and grew increasingly frustrated on days when I wouldn’t see him, and resentful that I wouldn’t sleep with him.

Even though I clearly stated I was newly divorced and didn’t want to be in a serious relationship, Dave refused to listen, choosing to believe that I was still romantically interested in my ex-husband. He broke up with me via text, finally citing that he felt I was not ready for any relationship, and definitely not with him.

Lesson Learned: Some men are needy and insecure, and stay clear of them. Also, don’t date men who text like teenage girls.

Date #3: Barry the Ice Cream Man

Barry took me to a great restaurant where we sat outside in the sunshine and I drank some delicious fruity drink. We laughed, swapped stories, and had a great time until he started talking (and laughing) about his DUI.

Lesson Learned: It’s okay to go out with a man once, have a good time, and leave on good terms knowing you won’t go out with them again. Also, if you do this right, months later when you visit his ice cream store, he’ll give you a double scoop of chocolate on the house.

Date #4: Shawn the Con Man

Shawn the Con Man deserved a story of his own. 

Lesson Learned: Listen to your gut. Not everyone is as great as they seem.

Date #5: Officer Jeremiah

Now that I had Homeland Security on speed dial, and had learned the art of checking references, I went on a several dates with Officer Jeremiah, a bonafide police officer. He took me out three times, and was not only fun to talk with, but the perfect gentleman. When I realized we didn’t have as much chemistry as I had hoped, he sensed this and let me off easy, telling me he understood if I wasn’t ready for a relationship only a few months post-divorce.

Lesson Learned: There are honest and generous men to be found in the world.

Date #6: Billy the Biker

Billy and I had emailed for about six weeks before we had our first date. He was smart, interesting, and fun – and a great kisser to boot – and I really didn’t mind that he wasn’t quite as good looking as his profile picture suggested. He had a Harley and I had dreams the wind blowing through my hair.

We had three solid dates before he blew me off for a while. Needless to say, I was confused and angry, wondering what I had done wrong, and started looking for someone better to date. When we reconnected a couple of weeks later, he was full of apologies.

I almost went out with him again, but by then I was sort of dating Date #7 and I had to make a choice.

Lesson Learned: In life you have to make choices. Make the smartest choice you can and then stick with it.

Date #7: Dave the Comic

An old co-worker set me up with Dave the Comic a couple of days after Billy went incommunicado. My friend texted me about him early one afternoon, he called me an hour later, and we met in person an hour after that. I didn’t even have time to get nervous because it happened so fast. We sat for hours talking after we had finished our food, and made plans to see each other the next evening.

Date number two went so well he wanted me to stay over, but Dave was a more than a little disappointed to learn I had no intention of sleeping with him. On date three he grew a little more surprised sex was not on the agenda.

I asked him what our friend had said to sell him on the idea of dating me. “He said he had a hot librarian friend I needed to meet, “ Dave explained. This is when I realized that my chosen profession is heavily stereotyped and Dave had a certain set of expectations based on those stereotypes.

Though I tried to compromise a little, he was frustrated that he couldn’t have what he wanted. I felt confused and unsettled by the exchange.

Lesson Learned: Trying to be someone I’m not to make someone else happy will not work for either of us.

Date #8: Barrett the Electrician

Barrett took me out on a great first date, followed a few days later by a second. I thought we hit it off quite well, and I wanted him to kiss me. While we played miniature golf, I threw out every signal that I could think of, used every flirty trick in my playbook, but he didn’t take the bait. Even though he told me he had a great time, he never contacted me for a third date.

Lesson Learned: Not everyone is going to want to date me, and that is okay.

Date #9: Poor Greg

I looked forward to receiving the emails Greg sent me for a couple of weeks before we decided to meet in person. It’s a good thing we didn’t wait longer and waste any more time.

When we met at a Mexican restaurant nearby, I knew within the first thirty seconds that there was no chemistry on my end (though, to be fair, I gave it three full minutes before making my final decision). I also knew within those same three minutes that he was interested in me.

I can small talk with anyone, anytime, anywhere, but dinner that night was painful. I ate two baskets of chips by myself just so I wouldn’t have to participate in the awkward one-sided conversation.

Lesson Learned: Sometimes you just won’t like him. And that’s okay.

Date #10: Terribly Dressed Jim

Jim asked me on a date after a few weeks of emailing, and we ended up going on three dates in four days. He was a nice guy, but he seemed to expect I was going to plan each of our outings (he was happy to pick up the tab, just didn’t have any ideas of where to take me).

There was one small thing that bothered me: two out of three times, he showed up wearing awful t-shirts – ones bearing giant wolves howling at the moon. It sounds picky and immature to judge someone on their clothes, but I knew if that bugged me, soon other things would follow.

Lesson Learned: It is okay not to settle.

Date #11: Socially Awkward Sam

I didn’t realize how socially awkward Sam was until a couple of hours into our first date. We met for a run – I was training for a 5k and he was an experienced runner – and I was so busy trying to remember to breathe and not die that I didn’t pay a lot of attention to what he said as he ran.

We went out for lunch afterward and it was only a few minutes into it that I realized that he was not only socially awkward, but boring to boot. I threw out every signal I could that I was not interested (including trying to pick up the tab), but he still asked for a second date. It took me six texts to politely decline, as he refused to understand my answer.

Lesson Learned: Be polite, even when you’re not interested, but be firm in saying no.

Not surprisingly, the novelty of dating had worn off during these months. I began to spend time out of work with Lance, who had recently (finally!) broken off his relationship. He needed some time off from dating and so did I; we decided we were just meant to be friends.

We took trips to the beach, made dinner together, got flu shots. One night he told me I was his best friend. It was the perfect thing Lance could have said to me; what girl doesn’t want a guy best friend? I figured we would stay like this: friends with an undercurrent of something electric.

A few weeks later though, after our third dinner together in a row, Lance told me he thought we should talk about us, that as great as our friendship is, we should really think about dating. “We’re practically dating anyway….”

Date #12: Lance(lot)

So I let Lance take me out on a real, official date. We went to an independent bookstore where we spent hours browsing and discussing books, ate lunch at a little cafe (he willingly traded half of his sandwich for half of mine), and took a long walk on the beach, talking and dreaming.

It was the perfect day, and perfect timing. Had we tried dating immediately after my divorce, we likely would have had several nice dates and gone our separate ways. Instead, we had six extra months of getting to know each other as I would report on each of my dates and solicit his advice.I had time to do the serial dating I had wanted to do; Lance had used the time to work on some issues of his own.

We were both now able to come into a relationship with clearer expectations of what we wanted and what we could truly provide the other, ready to build something substantial.

Lesson Learned: Timing is everything.

MORE: 10 Things Single Women Are SO Tired of Hearing (And How to Fire Back)

Amanda Stern

About Amanda Stern

Amanda never expected to find herself divorced, with children, in her mid-thirties. But she survived, and is now thriving, dating, and loving life. She is a cheerful optimist who loves to talk to strangers, marvel at the clouds, and plan her Halloween costumes months in advance. School librarian by day, she aspires to literary greatness, mostly by writing in her personal journal.

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