S.O.S-- Save Our Sanity: What The Fuck Is A Date?

At over 20 years of age, I find myself in a situation I have never, ever been in before.

I am getting ready for my first date.

Now, this may totally shock you. You may wonder how this is possible. You know I've had many men, and just a bit fewer relationships. No dates, you say? How is this possible? Let me explain. The men I end up with usually fall into two categories:

A.) I sleep with them, and then we continue seeing/sleeping with each other. (I.E-- Perfect, Legs.)
B.) They're friends of mine and we decide (most of the time, wrongly,) to take things to the next level. (I.E-- The Flaky Artist, Catholic Boy, The Inappropriately Aged Ex-Boyfriend.)

Dates are scarce things in these sorts of relationships. True, The Inappropriately Aged Ex-Boyfriend did take me out to dinner and a hockey game around our six-month, but, looking back, he was already cheating on me, and I get the feeling it was to try and mix things up and see if he could rekindle that (statutory) spark and feel bad about porking a fat 'ho behind my back. He didn't. I kicked his ass to the curb less than a month after when I found out about said 'ho. And then there were the three Kinda Dates that all add up to roughly one jigsaw-puzzle date: The Flaky Artist and I walked to the U Mall, where he bought me my double cheeseburger; Legs asking me out to meet for our tried-to-be reconciliatory coffee this past May; and my Chinese dinner out with Perfect...and Cait.

Hmm. See? No real, honest-to-God, getting-to-know-you dates.

But no. Now I have one this coming Friday night. And it's not with anyone you know.

You are so confused right now. I know. I'm sorry. The explanation of why Perfect is on bad-boy behavior back-burner status right now is in the works. For right now, this is what you need to know: We had a fight. It was nasty. It started about the care package, and ended in me drastically realigning his place in my life right now. It basically boiled down to him saying, "You're too serious about this," and me snapping back with "What could I be serious about? The fact that you're three and a half hours away and we never see each other and you're probably shacking up with half of the freshmen class females? Oh, give me a break. I'm just a tease, JUST LIKE YOU ARE."

Ahem. Pent-up issues are explosive when the fuse is lit. I may have finally reached the end of my leash with him, and became the equivalent of a chained, baited, and disgruntled/rabid pitbull of love. But, oh well. It's out, it's done, and I haven't heard from him in 12 days since the night of the Epic Fight, because I now refuse to be the only one calling/texting/Facebooking. Fuck it. If he wants to talk to me, he knows where to find me. I'm done with it. Moving on.

So, long story short, it's been raining men for me for awhile. I'm not trying to brag or complain, but it's has been damn eerie. First, Motorcycle Man resurrected himself from the Land of Thank God, I Think That's Over when I ran into him at a dance, or, rather-- he made his roommate come over and introduce us because he didn't have the balls to do it himself. I ended up giving him and his roommate a ride home that night since they were out a car and I was already giving another girl friend of mine back, since we all live in the same apartment building. I then received an onslaught of private Facebook messages from him, basically saying, "It was great to finally meet you; you seem like a really fun and chill girl; I think you're hot; come down and chill out with me sometime; I'd like to give you a ride on my bike before I have to bring it home for the winter."

...I would like a ride on that bike. But I played it safe and non-committal with everything else, ignoring the hard attempts, and instead just saying I was glad I could give him and his roommate a ride home, and life was really hectic right now. (No lie-- it's crazy-manic.)

But then, there's been this other interesting character, whom we shall call Gypsy-- and the enlightened of you can put 2-and-2 together and laugh if you know post-Medieval European slang-- sniffing around the edges of my life for, oh-- the past 2 months. He's about 5'10", with reddish-brown hair and great, crinkly blue eyes, and a body that is just-- yeah, it's WOW. (Think a young Aaron Eckhart. Really. Very much so. Alli and I saw someone running from behind this past summer and started making all sorts of lascivious comments about the guy's ass and legs, and as we drove by, realized it was Gypsy, who we only knew from the party circuit and were totally embarrassed and swore to never tell anyone we classified his ass as "chewable.") Every single girl I have ever talked to about him wants to bone him. Bad.

It started with a random Facebook friend request from him. Yeah, ok, we have a lot of mutual friends and I've chatted with him for a few minutes at a few parties before; I know he's not some crazy psycho-killer, so yeah, I accepted that request. And then he started commenting on some of my statuses, particularly the ones about running, since he's a runner, too. (Thought about calling him Marathon Man, because, hey, if the shoe fits, but no...there's a better nickname.) And then I started getting Facebook email messages from him at odd hours of the morning (AKA: drunk messages.) They were cute, they were funny; he's cute, he's funny, so I didn't think much of it. We chatted, basically. Gypsy is one of the most popular, good-looking, social, party-going guys in my class year. I chalked the interest up to Bud Light and runner's high. (And, oh yeah-- he's a Vermont Boy, too. Who sends texts that are identical to Perfect's, down to the exclamation points and "haha"s, did track in high school and loves exercising and sports, and had floppy brown hair until he recently cut it. Shoot me now. Universe, I hate you.)

And the Gypsy was at the dance, too. We happened to both be heading up the stairs at the same time for the door-- him to leave, me to get some air and cool down. (I be a dancin' FIEND.) "Hey!" I (ok, I'll admit it--) squealed at him.

"Hey, how are you?" he asked.

"I'm good! Hey, so you went to (enter South Vermont prep-school name here)! You know like, 5 of my friends who I grew up riding with!"

"Really?" Gypsy asked. "Throw me some names!"

I did, and we chatted from the bottom of the stairs through the door, or, basically, for about 2 minutes. In this 2 minute span of time, I realized a few things about myself and Gypsy and I.

A.) I am such a writer. Give me a screen or keypad to hide behind, and I am so much more comfortable. In email or text, I have time to plan what I want to say, and be witty and charming and flirtatious.
B.) In person, Gypsy and I act like the most retarded high school students you ever saw in your old high school's hallway desperately trying to connect with each other-- my voice gets high and girly, conversation flies out the window when we seize on something small and exhaust it in 2 minutes' worth of time and panic when we realize that one safe topic has been beaten like a dead horse, and we stare at each other for a bit until we realize we're staring, and then quickly look away. We are so awkward. It may be painful to watch. It's certainly painful to be a part of.

That night, when I finally got home, I found two Facebook emails waiting for me-- one, predictably the previously stated message from Motorcycle Man, and the other, from Gypsy. "I wish I'd been at least buzzed for that dance-- it was way too hot for sober dancing, haha!"

"Totally agreed," I wrote back. "I had a broke/sober summer, so now that I have a job any, any excuse to be buzzed is a good excuse. Also, a Thursday or Friday night time spot would have been nice-- a Wednesday is such an awkward day for getting your groove on. I never wake up and think, "Hey, it's Wednesday-- I want to dance my face off tonight!""

"Tell me about it!" Gypsy responded. "I found myself low on rent money and spending too much on drinks...what a horrible idea. You should pre-game heavy then get your groove thing on at Rasputin's tomorrow with me. I mean it is a Thursday. I know a good bunch of people are going. Can I just text you in stead of this silly FB message?"

I told him that unfortunately, I had previous plans (did not mention it was going out for the most hilarious of all double-dates that the Champlain Current has ever funded, bringing Nick and Anthony of "Flannel VS. Flannel," Alli and I for "Kitchen Bitches," and Henry, the Arts and Entertainment editor and a friend mysteriously nicknamed "Dos" to the Bobcat Cafe and Brewery in Bristol. I work with Anthony, who is a little bit psychotic in an endearingly scruffy way, and Nick is from Virginia and though he's lost the accent, still oozes Southern Charm and movie-star good-looks. I touched his cheek on the ride home to prove a point about how cold my fingers were and promptly almost swooned from the proximity and the perfect amount of stubble on his cheek.) but maybe some other time? I also gave him my cell number. Less than 5 minutes later, I got a text.

"Yeah," Gypsy told me, "that was my corny way of asking you for your number."

I responded back, saying it wasn't corny at all, and I give him props for not just coming right out with a totally uncreative "what's your number?" We texted until 1:30 AM, when we both went to bed. The next morning, after a meeting with a student, a work out at the gym, and distributing the second issue of the Current, I walked back in to the Current's Dungeon Office to hear my cell ringing. I picked it up and flicked it open to see a text from Gyp.

"You can't balance newspapers on your head for crap, haha!" he said. I was mortified. After working out like a mad-woman, my arms were dead beyond belief, and I had resorted to alternative methods of carting around newspaper bundles, including, yes, balancing them on my head like women from Africa do with their water. While standing in a campus building, newspapers on cranium, I specifically looked in the surrounding classrooms to make sure no one potentially damning could see me. One was empty. In another, everyone's backs were to me. And in the third, a girl/acquaintance from another class was laughing at me with her friend. Whatever-- Sami's a nice girl. We get along. She could get a good laugh at my expense in that boring class, and I didn't care. Who I apparently didn't see, but who had a seat next to Sami and watched the entire thing, was Gypsy, watching me try to balance 30 pounds of paper and newsprint on my (unwashed, previously had been sweating in a pony-tail that had since been taken out) head, wearing bright blue boy's soccer shorts that were still visible under my white Victoria's Secret PINK sweatpants, running shoes, a black tank top, and my new teal and black plaid hoodie with the furry hood lining.

"Oh my god," I texted back. "You saw that?"

"Haha...yeaaaaaaah."

"We're going to pretend that never happened," I told him. "But for the record, my arms were dead after just working out, so I was trying to come up with alternative ways to carry them. Plus, I'd like to see you do better. Do you know how heavy those things are?!"

I'm hoping this whole debacle was more quirkily endearing than hopelessly embarrassing. Gypsy has a playful and child-like side-- I'm praying it appealed to that side of him, and not the side going, "Dear god, I asked her out-- why did they ever let her out of the zoo?"

Anyway. Thursday night didn't work, so while I was in New Jersey this past weekend with my trainer, finishing helping her with the L Program, I texted him to try to set another time/happening up. Plan B, as I called it. Gyp said it was up to me; whatever I wanted to do. Technically, I know this is a guy being nice, but really-- guys, I hate this. If you let me choose, I'll try real hard, but I may choose something you hate. And then you're hating the date, which doesn't make it look good for Date #2. It's such a Catch-22.

At first I was thinking something festive, fun, quirky and memorable, like a corn maze, but my No-Free-Time schedule and his Equally-No-Free-Time schedule wouldn't allow. Plus, for a first date, it was kind of a hazard-- sure, if it goes well, you're together, alone, in a corn maze for a few hours as the sun sets. Endless talking time and getting to know each other. But, if it doesn't go well-- you're stuck in a corn maze together, hopelessly lost, as it gets colder and darker. That would be about when I say, "Thanks, but I'm outta here," and start bushwhacking my way out.

So we're doing the classic "grab a bite to eat downtown and stroll around the waterfront" on Friday evening. (I guess it's official-- it's happening on "Date Night Friday," so the cat is out of the bag to every person in downtown Burlington who sees us awkwardly with each other.) I'm already on full-on panic mode, even though by now, we have both mutually asked each other out once, and neither one of us has turned it down. If anything, Gyp is being really nice and attentive about this whole thing. But still-- I am a Philistine when it comes to dating. I am a ticking time-bomb. As I said to Alli when she asked, though he doesn't know it, fuck the date-- I would be willing to just stop, drop, and roll for him. I am liable to spontaneously combust, and I really need him to not know any of this. So, I'm stuck trying to cover all my bases before Friday, starting with the simple things, like wardrobe, and building up to the issues that make me squirm, like saying goodbye.

So, this is what I've got so far. The questions are what I need help with. And if you have any tried-and-true pointers, please, I would love to hear them. Like I said-- I've never, ever been on this sort of date where you sit across or walk next to someone and had to get to know them, figure out what makes them tick, or why they find me interesting/lovable/someone they'd like to fuck. (Some super Facebook creeping unearthed that his high school long-term girlfriend and I look similar, so that takes about a fourth of the "Why Me?" factor away.)

Wardrobe: It varies as of now. Until I get my hands on a weather forecast, it could be anywhere from a cute dress, scarf, cardigan and boots to jeans, flats, and a girly shirt. Whatever it is, it will be dainty, feminine, and a little revealing. I'm not totally stupid, here.

Location/Time: TBD. Somewhere downtown that's cheap and guy-and-girl friendly with the menu. And as for time-- after 4 and before midnight? That's broad enough for me. We'll narrow it down as we get closer.

Conversation: He went to high school with some of my friends. (Becky gave me some interesting info seeing as his ex was one of her friends. He can't stand flaky girls, and was/still is a bit of a player. Eh, whatev. You can't play a player, and Jay-Z might as well have penned "Ladies is pimps, too," for me.) We both go to the same college. We both live in the same town. (Sort of. He has a coveted Burlington zip-code.) We both like alcohol. We both have friends in common-ish. (His roommate went to high school with my roommate of the past 3 years, Melissa, and I've known him since freshmen year. Nice guy.) The rest-- the questions of getting to know him better; what's good to ask, what I should steer clear from-- that's where my blunt and no-holds-barred mind is at a loss. Heeeeelp?

The Three Times Rule: I am allowed to say I'll pay for my own food three times, says Alli. It goes something like this. "I've got mine." "No, let me." "No, really, I've got it." "I'd like to." "Are you sure?" "Yes. Please." "Ok, then. Thank you." (This is something I struggle with. Even when The Inappropriately Aged Ex-Boyfriend and I were together and we'd split pizza or Chinese, I had issues with him paying for it. Ok, so maybe not issues-- maybe like I can escalate this argument into a full on fight because, really-- why are you spending money on me? Although in total girl fashion, yes, if you will pay for it and are willing to reassure me of this fact numerous times, I'll let you. Unwillingly, but there is something hot about a guy who pushes my arguments aside the first time and hands the cashier or waiter money before I can protest again, I must say. Take-charge men. Yummy.)

"How Far Can I Drive This Car?" or Saying Goodbye: Hmmm. May have dug myself a hole with this night-time deal, because it allows for no easy outs, other than saying, "This was fun-- let's do it again sometime soon-- but I've got to go home now." Our stroll could turn into an invitation back to his place, which, let's face it-- it's getting fucking cold out in our little mountain state, and I get freezing so easily NASA could send me into space, no worries, but since I've already inadvertently played hard-to-get with having to turn down Gyp's first date idea, I'm seeing this thing through, the right way. I am about to become a girl who doesn't put out on the first date. As Alli, and Becky, and my own thoughts, memory, and intuition have warned, Gyp can be a bit of a player. And dammit, he's gonna work for it. First date= kiss goodnight. If it goes well. If he's lucky. If I don't just turn tail and run away, because I am notoriously nervy about first kisses.

So, that's where we're at. I'm not a total mess-- I know not to lick the plate like I can get away with at home with Melissa and Alli, and I know not to ask any dreaded Ex-Files questions or talk about babies and marriage. (Neither of which appeal to me AT ALL in the first place, so it's a safe bet anyway.) But still. I am a freaking 20 year old date-virgin. I have a date Friday night with the Hottie of Junior Year at Champlain. I have a habit of making an imbecile of myself in front of him. Let's just hope he's got a thing for imbeciles, or, really, really smart girls who just can't get out of their own way. All aboard-- this is one hot mess!

But really, I'm excited.

...Sure I'm going to vom, but excited.

As I said to my trainer, "...So you can suck my dick, Perfect." (Totally texted Cait and let her know about it so she would tell him. Bwahahahahahahaaaaa. Eat it. Eat it, Tease Boy.)

Onward. Upward. Gypsy-- get ready, because you have never met anyone quite like me.

XOXO