When the Chips are Down, Wager Boldly

At an outing with coworkers on Friday afternoon, I revealed that I would not be attending the company Christmas party because I was attending the holiday festivities of The Engineer's workplace. It was a fine trade-off with me in most respects; I'd planned to attend the ATown office Christmas party on Friday, so missing the big shindig in Hotlanta didn't sadden me too much.

The revelation was followed by a million questions about The Engineer, and I was honest with them in saying that I was undecided as to his fate in my love life. And that in general, I was exhausted with dating and ready to wash my hands of the whole evil business. That's when things got interesting.

RK, who is part-owner of the firm, threw a $20 bill to the bar floor. "That's $200," he yelled. "It's $200 on you."

I looked at him open-mouthed, wondering what he was all fired up about and finding it hard to take the $20 seriously where it lay beside his pedicured feet with their alternating red and green toenails. That's his lot in life for offering an outing of our choice to a bunch of ladies.

"What are you talking about?"

"I'm putting $200 on you. And I may up the ante, but - let's record this," he barked.

One of my coworker dutifully dug out her iPhone and urged him to continue. "Today is December 9, 2011. And I'm wagering that in two years - TWO YEARS FROM RIGHT NOW - Ashley will be engaged. Or I owe her $200."

And that was that. I picked it up the $20 bill, looked into the iPhone and yelled, "I'll take that bet."

It's on, people.

A Disasterous Run at Having a Love Life

It is a truth universally acknowledged that an Ash in want of a boyfriend is an unmitigated disaster. As proof, I give you the shambles of what one might call a love life if the string of sordid events from the past year outlined below could even pretend to assume such a likeness.

• The CPA - Delivered to me on 29 points of compatibility - two of which I've come to believe are "human" and "alive" - The CPA and I made it through the four stages of online communication like two cadets on the obstacle course of dating. And in real life, when we met, it was...boring. Our chemistry was like all the lab experiments I was forced to perform during a summer chem course - unresponsive and a complete failure in producing the expected reaction. We hugged gamely at the end of the evening and never spoke again. Truth be told, I can't remember his name.

• The Zealot - With the trappings of all normal people, The Zealot was also funneled into the pipeline by Dr. Neil Clarke Warren's evil machinations. He was affable if a bit overly nervous, polite if somewhat solicitous, and attentive if only slightly creepy. He "we'ed" a lot and there was a strange preoccupation with his married friend whom he wanted to emulate down to the point of buying a house in the same neighborhood. It wasn't until he insisted that our third date take place on Valentine's Day that I truly began to notice the red flags. And when he showed up at said third date which I insisted be on another day (any day for the love of God) other than Valentine's Day with a pink bag frothing with tissue paper and containing a mixed CD complete with meticulously compiled liner notes, I drew the line. As in the line of communication. And I cut it.

• The Old Friend - In the midst of my fruitless online search for someone new, someone old emerged from past. An old friend, a college friend. We never dated, but I harbored a latent crush while we both dated other people. We lost touch and reconnected over the years, but after a profound and prolonged silence, there was suddenly the magic of Facebook to bring us together again. And soon I was embroiled in an intense texting affair and then a roadtrip, all of it doomed. I knew before it began that it would be over. And then just like that...it was.

• The Paper Boy - Doubly burnt by the eHarmony's dimensions of compatibility (which seemed to include the Twilight Zone), I quit paying to be sent out on bad dates and looked a little closer to home. The Paper Boy and I had been acquainted for going on a year, having found a mutual love of Counting Crows, barbecue and biting sarcasm. We were chums - dude friends, if you will. Until we weren't. Until one night when we were leaving a concert, and it was cold and he put his arm around me a pulled me into his coat to keep me warm. And then he asked me on a date. It took weeks to schedule because of our respective business travel, but the date was pleasant and fraught with anticipation until it ended abruptly when we arrived back at my house to find my visiting friend asnooze on my couch. Ouch. But a second date never really happened as we entered some strange game of cat-and-mouse until I finally called him out on his behavior (after a couple of strong gin drinks), and he confessed that despite his declarations to be moved to date me, he found the idea less palatable in practice. The office sent me flowers of mourning after that particular disaster.

• Dr. Feelbad - We met on Halloween. I was dressed as Shirley Manson, clad in fishnets, a micro-dress and a can of hairspray. He was dressed as the devil. (Like that shouldn't have tipped me off...) I flirted outrageously - he was tall, dark and sexy. I was sort of dressed like a hooker. A Ph.D. candidate, clearly smart, he made quirky sophisticated jokes and looked impeccable in a three-piece suit. He got my number...showed up at my tailgate on Saturday and then met me out for drinks later (after which he took me home...and once again, I had a house guest. Note to self: STOP ENTERTAINING). The following week we took the texting route of flirtation. I met him with a group of his friends for drinks. And then...finally...he asked. "Let's do something tomorrow - movie, your place." After work the next day, I sped home, cleaned the house and was sitting calmly on the couch in a rather fetching outfit that said relaxed but tempting when I received his text message at nearly 8 o'clock letting me know he had friends in town and did I want to meet them out for drinks later. Dear Captain Blowoff: suck it. I haven't heard from him again.

• The Engineer - Despite my failed attempts at online dating before, I decided to return to it. Only, if it was going to be rife with failure, I was going to do it for free. I joined OkCupid, which, along with its other free counterparts like Plenty of Fish, is a get-what-you-paid-for-endeavor. The searching is sketchy at best, and the matches presented on your home page may have absolutely no compatibility with you whatsoever. You're likely to be solicited by married people in open relationships and drunken college boys looking for a gameday hookup (ewww). I have literally been addressed as "Ms. Hot Rod" in an email from this site. So that's how I met The Engineer - the least creepy and even - dare I say it? - almost promising match! We met, and he was, in fact, not creepy. Bonus points: he was attractive! And now we've been on several dates, and I'm in that awkward phase of trying to determine my next move with this guy who has made no bones about not wanting marriage, children or to live in this country for that matter. Because, even now, even when I found someone I might like to date, it can't be easy. Where would the challenge be in that?

Lest you think this list is comprehensive, I'm leaving out the guy who I met online under an assumed name who turned out to be recently divorced and looking to flee the country. Or the guy who professed his affection for me after a date I didn't realize was a date and didn't want to be a date. Or the preacher's son who is a cop and a known profligate who has suddenly started texting me.

And please don't slap me with the admonitions that I will find someone because there is someone for me and I have to kiss a lot of frogs and I have to be patient and-

Seriously. Don't. I acknowledge all those things. But I direct your attention to the above...and you can't argue...that it pretty much sucks. Am I right? I thought so.