Courtship Connection: If At First You Don't Succeed, Try to Get Her Wasted

Since the dates in D.C. have been a little more exciting than those in Chicago, Kash decided to spoil you with one last set-up in the nation's capital. She brought in a pinch hitter for this one. The two legal eagles both sounded like thrill-seekers to her, so she sent them to The Russia House after work on a Friday and hoped for an epic night. Epicness ensued....

Since the dates in D.C. have been a little more exciting than those in Chicago, I decided to spoil you with one last set-up in the nation’s capital. I brought in a pinch hitter for this one. After a “disarmingly feisty and unabashedly vivacious” female lawyer shot down the frat boy I set her up with, she asked to be set up with someone more her type, “aka really hot, quirky, and a commitment-phobic womanizer.” Pinch Hitter emailed me, saying he fit the profile.

Feist-Master said she was up for round two, but then disappeared off of the face of the earth email. So I decided to pull a switcheroo, pairing the quirky commitment-phobe with another of the many single female lawyers in D.C. I chose a hot, young T-14 grad at a Biglaw firm, who self-described as “optimistic, spontaneous, and active,” and said she would be a journalist if not a lawyer. The two legal eagles both sounded like thrill-seekers to me, so I sent them to The Russia House after work on a Friday and hoped for an epic night.

Epicness ensued. This is the kind of first date story that Wannabe Lara Logan will be able to milk for years…

Wannabe journo said she’d be carrying a yellow umbrella. Our womanizer said he would be in jeans and a button-down with “Screech-esque, dark, curly hair.” Nice move, womanizer. Compare thyself with a decidedly unattractive character to set expectations low and display your humility. Bravo. Though, if you actually look like Dustin Diamond, I would advise against this tactic.

Yellow Umbrella says:

As promised, he had curly hair like Screech — in fact, he really did kind of look like Screech, but not in a bad way — sort of like when Urkel used to go into that machine and come out as Steffan on Family Matters — just an overall resemblance.

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Points for a reference to Stefan Urquelle, Yellow. Was ‘Sam Powers‘ as charming as Stefan?

We ordered some drinks and got to talking — he went right for the “What do you do?,” which would not have been my approach, but fair enough. He continued to ask such getting to know you questions in pretty rapid succession, about my family/interests/school, etc. I honestly would have preferred to let conversation flow more naturally, but it was pleasant enough, and we did eventually get around to some more interesting stories/common interests.

Uh-oh, bad move, Hot Screech. She’s a wannabe journo; she wants to be the one asking the questions. He says:

I headed home from work on Friday at about 5:30 and, along the way, several presumably not uncommon realizations began to hit me; namely, I had never been on a truly blind date and I had also put all my faith in the matchmaking abilities of someone who knew almost nothing about me or my date and who, despite potentially altruistic motives, realistically only needed to be assured of getting some entertaining material. It also occurred to me that, inadvertently, this might have become the most highly-anticipated date of my life since more than six months had elapsed between the day when I first e-mailed my Courtship Re-Connection proposal and the day when the action was finally about to go down. But I also reminded myself that I was in the advantageous position, or so I thought, of having some material to work with — my date’s exceedingly amusing review of her painful prior Courtship Connection had been the impetus for my proposal. Plus, I had reasonable confidence I could make a pretty good run at most of what “disarmingly feisty and unabashedly vivacious” had been looking for and was very enthused with the prospect of “a [hot] lawyer with a high tolerance for alcohol and a low tolerance for boredom.”

This is the part where I started to feel guilty.

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I got back to my apartment about with about 45 minutes to spare. While I was changing and was considering whether to wear a particular faded pastel Hawaiian shirt which was purchased at a truck stop in the late-80s (among my friends, this shirt has become somewhat infamous as both a deal-breaker and a deal-maker in the past), I began to consider the particularly high value I place on two essential dating tools — (1) Facebook, because, admittedly, a sneak preview is the only way to prevent against the prospect of spending several hours across from someone to whom I am not in the least bit attracted (not a problem if I want a new best friend, but a big problem if I want to find someone I’m excited to date); and (2) booze, because it is the ultimate temporary beautifier, “rule” nullifier, and facilitator of scandalous behavior. With Facebook proving useless in this case, there was only one way to prepare, get drinking. This approach quickly led to three drinks, the last of which my cab driver almost made me dump until he took sympathy on me because I told him I was headed to a blind date that was going to be blogged about shortly thereafter for thousands to analyze and judge.

Three drinks in an hour? I have frequently endorsed healthy consumption of alcohol on a blind date, but it’s best consumed with your date, not alone.

So now, Kash, comes the part where I discovered that you are a master baiter-and-switcher. I was pleased to see that my date was cute, around my age and seemed fairly athletic. She was also quite nice and intelligent. However, I was not so pleased to find out that she was not Ms. Disarmingly Feisty and Unabashedly Vivacious. I’m not sure how well I hid my initial surprise upon discovering the switch but I did try to recover… a few gin and tonics really helped the effort. The next few hours were relatively typical small talk, mostly me asking questions to try to keep the conversation going.

Honestly, I thought I had conveyed to him that Feist-Master had stopped responding to my emails. Perhaps I didn’t… or perhaps he received that message while in some kind of drunken haze…

The Non-Feist-Master says:

I knew almost right away we wouldn’t be a romantic match, but he seemed like an extremely friendly and fun guy. He also much faster/better drinker than I was — he later mentioned he had requested a “smokehouse, not particularly interested in being a lawyer, and a boozehound.” While I had never heard the first term before, I definitely fit the second, but totally fail the third request.

UPDATE FROM SCREECH: “Disappointed that she screwed up the nomenclature: ‘smoke[show]’ is desirable, ‘smokehouse’ sounds like an old woman who smokes a pack a day.”

From the beginning I felt like he was more into creating a great “date” story than anything else — stopping at several points to stage a photo op for the blog, mentioning how the date had to be either “awesome” or “totally awful,” and even texting me the next day that we had created plenty of “fodder” for ATL. He even admitted he emailed Kash during a trip to the bathroom to tell her so far so good. (Really, Kash, I think he might have a crush on you — he kept mentioning how he didn’t want to let you down).

I never received said email. I received an email that said, “Kash, you sold me out, still on date but this is not the midget stripper, in need of a womanizer girl.” But maybe that was drunken-haze-speak for “this is going really well.”

He had a theory that all the prior Courtship Connections that had gone wrong were because the guy seemed just “average” — in fact, he admitted he had first gotten in touch with you because he wanted to launch Courtship Reconnections, and go out with a girl who had bashed her previous date — he was initally under the impression that this was my second time going through this, and may have been disappointed that was not the case.

Yellow Umbrella is perceptive.

Hot Alcoholic Screech says:

I was fairly certain my date was headed nowhere promising and I was ready to head into my other Friday evening plans which primarily included what promised to be a raucous going-away party for a good friend who was headed to the U.S. Virgin Islands for a judicial clerkship (tough life). I was just about ready to part ways and had started the obligatory questioning about what her plans were when it hit me that I could not just let this go down like the overwhelming majority of the other Courtship Connections. At the same time, it occurred to me that if I could get my date to rally some cute single friends to bring along to my buddies’ party, chances increased significantly that at least someone might get to hook-up out of this deal — to my surprise, she agreed.

At this point in the date, Screech launched “Operation: Get Her Wasted.”

Given her general demeanor and the reality that I know few folks who party as aggressively as my group of friends, I was pretty sure that without more booze, my date was highly-likely to be overwhelmed by what she was about to walk into. So, being an advocate of a firm policy of escalation and wanting to allow her reinforcements to rendezvous before I threw us into the party mix, we walked from Russia House to my buddies’ place in Logan Circle and stopped for a few more shots (see picture) along the way. At this point, it was very clear to me that I was (1) likely to get destroyed by the end of the evening; and (2) almost certainly going to get worked in her ATL write-up. But oh well, if I ensured the former, maybe I wouldn’t care about the latter.

She says:

Anyways, after that, we agreed to head out to another bar he used to bartend at, and we got some drinks there, along with some shots from his bartender friend (the shots were a surprise, NOT my idea). He had mentioned that a bunch of his good guy friends were having a going away party, and I had agreed to stop by, always willing to hang out and meet new people.

Translation: maybe this date can be salvaged if he has a hot, non-alcoholic friend.

We stopped at another local bar (his “spot”) to grab a drink while we waited for one of my friends to meet us, and then headed to his friend’s apartment soon after. At this point I had stopped drinking, pawning off the drink he bought me at the last bar on my friend, and declining the jungle juice equivalent at the apartment.

At some point in the night, they seem to have time-traveled back to college. Screech says:

We arrived to the party somewhere between 8:30 and 9:00, I think. Admittedly, this is just about where things got interesting and where my memory begins to fade. The next several hours involved about thirty folks demolishing a keg and about 6 gallons of John Daly’s (sweet tea vodka mixed with lemonade), multiple rounds of beirut (to my date’s credit, she played quite well until we both fell apart following our third consecutive win), and general drunken absurdity. My date had managed to rally one friend, but she was clearly not cut out for these shenanigans and bailed after about 45 mins and some short conversations with a few of my friends.

I’ll be curious to hear the degree to which I behaved badly during the final hours of the evening but I can tell you that although my date got “leid” (see picture), it did not involve the removal of any clothes.

We’ll let Yellow Umbrella pick up where Screech’s black-out begins:

His friends were a very enjoyable group, and we played some beer pong (I made him drink all the beers, perhaps pushing his drunkenness a little over the edge), but eventually I really reached the end of my willingness to hang out and was trying to find a way to exit when [Screech] decided he wanted to get food. Since the place he wanted to go to was on my walk home, I agreed to head out with him; I was a bit annoyed upon arriving at this last bar that instead of getting the water I requested, he ordered me a vodka soda and insisted I drink it (I did not).

At this point, he must have realized that “Operation: Get Her Wasted” was not going to involve a “Mission Accomplished” banner. Still, he forged on:

He got his food to go and we left the bar; when he asked me where I was going next, I pointed in the direction of my apartment and said that way (he lived in the opposite direction). He then basically flat out asked me to go back to his apartment, and upon my denial, said “you can’t blame a guy for trying” — to which I responded, “yes, yes you can.” I wasn’t really offended, but at this point, was really ready to be home and pretty much done being nice. He kind of took me by surprise and planted a kiss on me. I didn’t know how to react and kind of just walked away afterwards; he was pretty drunk at this point, so I’m not sure what he was thinking??

Probably: “Girl. Pretty. Kiss Her. Maybe she go sex with me.”

Beyond The Call Of Duty says:

I think I should have left much earlier in the night, and perhaps not led him on, but like I said, I felt this pressure to live up to this “awesome” date he wanted to have. He truly is a nice guy, but we got along in the way that any two normal, sociable adults would—no real chemistry or deep conversation, just general hanging out.

Creepy Screech remembers it a little differently:

In the end, I think we parted ways around midnight with no fireworks going off. There were some texts exchanged over the next several days, but these were mostly sent at the urging of my date and a buddy, for the purpose of setting him up with the friend who had left the party early. (Note: this connection has also since run its course with a complete absence of fireworks).

Screech has some advice for future Courtships:

I think the idea of setting up lawyers with lawyers has some real promise but only if the right types are matched. I have the sense that there is the type that truly embraces the “work hard, play harder” mentality, and the type that prefers “work, work, work, and play if and when possible” (e.g., where “play” may entail martini parties or a lot of wine and cheese tasting adventures at vineyards without even the brief thought that this could or should actually be followed by some scandalous behavior amongst the vines). I firmly believe in the “to each, their own” philosophy and see benefits to both lifestyles, I’m just more the former type and tend to shoot for the same in a match…

(Disclaimer: I realize that much of what I’ve written involves the excessive consumption of alcohol. I blame this behavior on the legal profession and four years at a small liberal arts college stuck in the middle of corn fields).

Apologies to you both for the bait-and-switch and the setting-you-up-with-an-inappropriate-boozehound, respectively. Meanwhile, I shall send this write up to Unabashedly Vivacious and see whether this ‘play hard’ match appeals to her after all.


Kash is an editor emeritus of Above the Law. She now spends her days at Forbes writing about privacy, technology and the law at The Not-So Private Parts. For a background on the creation of ATL Courtship Connection, see My Weird Hobby: Matchmaking Lawyers.