Call Me Miss Insecure

I'll be blunt. Dating Mr. Charming has reawakened a part of myself long since forgotten, a part of myself that I absolutely, uninhibitedly do not like: the insecure part.

Before anyone jumps to any unsavory conclusions about the man in question, this is not his fault.

…unless you're blaming him for the fact that I like him, in which case, what a bastard.

But short of that, this is mostly down to me, and perhaps a little bit of the blame also lies on the men who came before. Oh, and absurd gender roles that society has forced on us.

You see, after that oh-so-charming first date with Mr. Charming, I found myself in unfamiliar territory. I was stuck waiting around to see if he would ask me out a second time. This might sound incredibly arrogant, but the truth is I haven't been in this situation very often. Most of the time, as you're well aware, I feel lukewarm at best about a first date. It is a rare occasion that I go beyond a second date with someone. The select instances that I have, I've been sucked headfirst into a hurricane.

For the record, this nearly always turns out to be a mistake. The primary examples are the infamous Misters Manipulation & Mess. Here's an overview:

Mr. Manipulation asked me out on about four dates within the first five days that I knew him. Part of this was inspired by the fact that my schedule that month meant I wouldn't have a chance to see him again for another two weeks. I was flattered and felt pursued and desired, a feeling I was (whether you believe me or not) almost entirely unfamiliar with. My head got turned. By the time I got home from 14 days of nearly non-stop travel, he immediately asked me to be his girlfriend. I was taken aback and hesitated, as I hadn't been expecting this so soon. When he saw me falter, he started to withdraw the offer. "I'm not going to ask again," he said. I immediately played into his hand and accepted, fool that I was.

The situation here boiled down to two things, in my opinion. He did not like that while I had been away, we were non-exclusive, and that I had a right to do whatever I wanted with whomever I wanted. Not that he'd had anything to be worried about—I'm a one-at-a-time kind of dater—but I have no doubt he was anxious to exercise that control over me. The second reason is that Mr. Manipulation was eager not to have to work at wooing me anymore. So far as I can tell, he believed that once we were in a relationship, he no longer had to put any effort into winning me over or making me happy. As his girlfriend, it was my responsibility to be at his beck-and-call and to please him.

Mr. Mess, on the other hand, was never meant to be a serious relationship. I had known him for about 7 months when we started spending real time together, and the wheels were already in motion for my move to Chicago. With the pre-existing comfort of already knowing one another, we easily fell into what was meant to be a summer fling. I intended to enjoy some quality company before I kicked South Florida's sand off my flip-flops, and I didn't see a point in playing coy or hard-to-get since time was limited.

In retrospect, had I known that we would make an attempt—however brief—at a long-distance relationship, I would have proceeded with more caution. Though he treated me with a kindness I was no longer accustomed to, Mr. Mess had some serious issues, including a tendency for depression and a crippling fear of failure. I was vulnerable after Mr. Manipulation's mistreatment, and I overlooked these things until inevitably they blew up in my face.

So rationally I know it's a good thing that most things with Mr. Charming are going at a more leisurely pace.

But it's been a really long time since I've been in this position, constantly checking my phone à la Gigi in He's Just Not That Into You, because somewhere along the way society made up the rules that the woman has to play at aloofness or risk being seen as forward or desperate or, God forbid, attainable. Stupid, of course, but still a reality.

My friend Clive does not understand this. Apparently, for gay men, the so-called rules are entirely different, and he spent the entire third day yelling at me.

"Just text him, for God's sake!" 

Which, to be fair, I already had. After the Minty-Fresh Date, Mr. Charming said I should let him know how my trip was going for work. And I did. Twice. And he texted me back. And we flirted a tiny bit. And then the conversation fizzled out both times, so I decided I should let him reach out to me next.

And so three days of agony passed. Three days of my roommates and Clive all being absolutely beyond fed-up with me whining about why he hadn't messaged me and how he must not have been as interested as I had thought he was.

Then, one hour from the exact moment that I had given up on him, Mr. Charming asked me on date #2.

Aaaaaaaand then it all repeated itself for date #3. After which I realized I have got to calm the fuck down and stop convincing myself that if I haven't heard from him yet, it means he's out.

For starters, if he does lose interest, so what? Yeah, I like him, but life goes on and plenty of fish in the sea blah blah blah whatever.

Second, he has given me every reason to believe he is interested, and this thing that's happening where a few days pass and then he decides to ask me out again, that is normal. This whole thing is completely normal and I really, really need to get a grip. I'm almost ashamed of the amount of time I have spent fretting over whether or not my company is actually desirable.

Considering that I find confidence to be one of the sexiest traits in a man, I think I need to tell my own insecurities to take a hike. After all, if I wouldn't want to date me, then why on earth should I expect anyone else to?