A wise Mind of Man once told me, “Generals are always prepared to fight the last war.” People—well, OK, I—try and work through the crap of their last relationship with the person they’re with currently. This, I think, explains why, for the better part of my adult life, I have been a complete and total spaz when it comes to men and dating. I know, shocking right? if I was a spaz before the relationship with my ex-fiance, I was a complete and total bunny boiler after he broke up with me. I was an insecure, over-analytical nutter and wasn’t sure how, when, and what it would take for me to stop fighting a war in which I was the only participant.

The last time I went on a date was a month ago and it was decidedly “meh.” I deleted my profile off OKCupid because I was sick of getting new messages from guys who were, at best “meh,” at worst psychotic/illiterate/pervy. To be honest, for the first time since my breakup, I have been enjoying being single. And I don’t mean single as in “I’m dating lots of guys and going out all the time like Samantha from ‘Sex and the City,’ woo-hoo!” I mean I am single and enjoying my alone time.  I’m having dinner with friends, catching up on movies I’ve missed (I think I am the last of Blockbuster’s customers), riding my bike, and starting up yoga again. Next month I’m going on a yoga/surf retreat in Costa Rica for a week, and when given the option between coed or an all-women retreat, I went with the latter. Coed shouted two things to me—couples (blech) and single dudes looking to show off their shredding abilities. The latter would normally kind of turn me on, but like I said, MEH.

A few weeks ago I wrote about how I wasn’t sure if I was really ready to be dating again, that I was still dealing with the lingering effects of my last relationship in which my fiance ended things suddenly.

“...I desperately fear, in all sincerity, that I will never again find someone who loved me like my ex-fiance did. And that even if I do, they will likely leave me the way he did. Isn’t that pathetic?”

A friend of mine emailed me, specifically about that line, saying it wasn’t what she expected to hear me say.

I have a confession to make. I hate dating. Except for when I love it, and I only love it fleetingly, before my insecurities set in and I start to go cuh-razy. In those fleeting moments I think to myself, “This is great! I’m young, I’m unattached, and there’s an attractive person sitting across from me who I may or may not make out with later.” And then later, after we have or have not made out, the wheels start turning, and I begin to wait for the inevitable letdown that, as cynical as this may sound, I assume is right around the corner.

Lately I’ve been getting a lot of advice. Solicited, unsolicited, much of it from female friends, most of it contradictory. Many of my female friends are in relationships, including my four closest girl friends, two of whom are married and two who are headed in that direction. They all are living vicariously through my “dating adventures,” though I’ve tried to tell them that it’s about as exciting as a bowl of oatmeal.

People give advice based on their own experiences. What works for them has got to work for you too, right? Like following a cake recipe, if you follow the right steps, you’ll get the end result you want. Except dating is nothing like baking and there’s no “right” way when it comes to matters of the heart. I watched “He’s Just Not That Into You” this weekend (out tomorrow on DVD) and if there’s a takeaway from that movies it’s this: everyone has a dating tale that is an exception to another person’s rule. Which is why all of the advice I’ve been getting has been making my head spin.

I have been thinking for the last few weeks that this nonsense with Chicken Parm had to end. It had been over practically since it began, although I was the last to see it. He was the first person that I had truly strong feelings for after my breakup, but he was my rebound. As much as I wanted it to be more, probably for the wrong reasons, the timing was wrong for him and wrong for me. It didn’t help that he was the worst person to date, in that we didn’t actually date. That was partly my fault; never again will I cook for someone so early on. My chicken parm isn’t that good, but apparently my nurturing instincts are, and we went from hot ‘n’ heavy dating to sexless marriage in no time flat. 

Last week I had a new OK Cupid date, this time with someone who fit my type. You see, I have a type that I wish were my type: guys in plaid, guys who are sensitive, guys who look like they’d be friends with Ryan Gosling, guys who are over 5’9”. And then I have my real type: the guy who I’m inexplicably drawn to and drawn to me, too. This type of guy is dark-haired, under 5’9”, and extremely confident.

This latest guy (let’s call him the Sneakerhead) fit my type to a T, but he had some bonus features: a cool sneaker collection (you can tell a lot about a guy by his shoes), a good tan (a product of his half-Argentinian ancestry), he was a hip-hop fan, and he wears glasses. Oh, and he has a tattoo. And he doesn’t have a doughboy body. He’s my real type, plus perfection.

I never thought I would be in the position of dating with a broken engagement under my belt. I hope to never have another. As I’ve started dating again, I’ve had to think about how honest I want to be about my prior relationship history. So, how honest do I want to be? Totally.

At first, I thought that I had been engaged might work in my favor. Men are inclined to assume a woman is more interested in something serious than they are, that women want more from men than they’re ready to give. After all, women are always a little further ahead on the marriage path, aren’t they? But I was engaged and dumped. I’m newly single. Therefore, I must project a “just looking to have fun and meet new people” vibe, right?

Apparently not.

To be honest, I haven’t been in the position of rejectee very often. I dated this guy in college for a couple months who one day showed up at my window in the middle of the night, rapping on my window, asking to be let in, because he was running from the cops. (I’m still not sure why). The next morning when I drove him home, I called it off. I was 19 and in college. He was 27, working at a crappy seafood restaurant, and had no problem running away from the cops in the direction of his girlfriend’s house. It was not going to work. I told him that, and he got very upset, but I felt a huge weight lifted off my shoulders.

Another time I had a torrid, two-week affair with a man who was 12 years older than me and a pathological liar. When I found out, I had no problem screaming at him and telling him to never contact me or breathe my name again, lest he want me to ruin his life. That one was easy. But, in general, I find letting someone down to be a difficult thing to do. Maybe that’s why I should be a little more sympathetic towards men when they give me the runaround rather than telling me straight up: “I’m not interested in you like that, despite coming over to your apartment after our date and touching your boobs.” But I’m not sympathetic. Because sometimes in life you have to do something that is uncomfortable but necessary. Telling someone straight up how you feel in an honest but gentle way is one of those things, and giving him signs, pulling “the fade,” or just disappearing altogether are not acceptable substitutes. I forced myself to remember that today, as I told Mr. Plaid Glasses that it wasn’t gonna happen.

An update on the Doodler. I do no like, nor do I accept, guys sending mixed messages. According to He’s Just not That Into You, I’m supposed to read the signs and accept, without a guy actually saying so, that he’s not interested. But the Doodler left me confused. He seemed interested! We hooked up! He’s roommates with one of my friends! Besides, we had fun, didn’t we? Why wouldn’t we go out again? I emailed the Doodler on Friday evening, suggesting we go out this week. I haven’t gotten a response. Rude much?

As for Chicken Parm, things have been rather nice between us the last few weeks. Friday evening, Chicken Parm came over, not to spend the night, or go to dinner, or even to screw. No, he came over to nap. And cuddle, too. Then, he left. Last week, he told me, “I wish we lived in the same building but had separate apartments, so I could do work in mine, but sleep in yours.” It was oddly romantic. I think I may have even said, “Aww.”

Ugh, ouch. Copious amounts of red wine and very, very, very tiny plates of food – genius way to get your date lubed up.

So, last night I went on a date with this guy – oh, let’s call him The Doodler, since he’s an artist – that a good guy friend of mine set me up with. While being set up with a friend of a friend has its drawbacks – like, what if the date goes terribly and you have to avoid each other in the future? – I really like getting that stamp of approval from someone I trust.

Before I get into the logistics of the date, a note about artsy guys. They are so much more attractive when they’re ambitious and gainfully employed, rather than starving and lazy. It also helps when they’re actually talented, which The Doodler is. Thank goodness. There’s nothing more awkward than dating someone whose art/music/writing you hate.

For the last few months I’ve been seeing someone – Chicken Parm, as he’s been referred to a few times already—that I met on the online dating site OK Cupid. I signed up for the site on a whim on New Years Day, as I was recovering from my hangover. New Years Eve was the last in a series of breakup milestones, as it would have been my fifth anniversary with my ex, and the first anniversary of our engagement.

I signed up for online dating because I felt officially ready to date again and what better place to find likeminded men than on an online dating site?! Chicken Parm sent me a message and his profile instantly intrigued me. Of the three adjectives he used to describe himself, one of them was “hungry.” I had wanted to describe myself as hungry too, but balked out of fear that it would imply I was hiding a huge ass beneath my head shot. His taste in music was a mix of artists I loved and stuff I’d never heard of, and a lot of hip-hop, which I adore. He was cute and he tanned well. Reply!

As many of you who have been reading The Frisky for awhile know, I was engaged for much of the site’s lifespan. I was with my fiance for four years when he proposed on New Year’s Eve 2007. I wrote about being engaged for The Frisky in a regular column, “So I’m Engaged.” When he suddenly left me last September, I was, frankly, devastated to the point where I could not get out of bed. I missed a week of work and lost about 10 pounds. I felt absolutely mortified by the existence of those “So I’m Engaged” columns and couldn’t stand the thought of anyone reading them. They felt like the words of someone in a one-sided relationship, and their existence hurt me and embarrassed me. So, I took them down.