Multi-date Update (Specifically: #6, #2 with #4, and #7)

I’m not going to sugarcoat it. I’m highly discouraged. I’ve primped, primed and pouffed my way through more than a handful of men and nobody has yet to float my boat, as they say. Yes, I’ve had the sweet, the successful, the adventurous, the handsome, the brains — even the quirky and unique — but no one has weaved these together into a harmonious package that catches my eye as it twirls and sparkles in the store window.

Before I wallow in my self-prescribed misery, I owe each of the last three dates a paragraph or two to make their case…

The scene: Cafeteria in downtown Uptown on a busy Tuesday night. The dude: 36-year-old Rich — a man wafting of come-hither cologne and one-button-too-many-unbuttoned coolness. Why it would work: If I wanted to spend my days golfing, schmoozing and pretending I’m ten years younger than my real age, we’d be fantastic together! Why we just can’t work it out: Rich, who was rich (did I mention he was rich? He would let you know if I wasn’t making it clear), was just not my type. Interested in slick cars, coasting on well-timed career success and partying like it’s 1999, he was smoooooooooth. Intimately absorbed in keeping his tan just slightly orange enough as to let you know it was fake — and totally untrustworthy. Next, please!

The backdrop: Urban Eatery overlooking Lake Calhoun. The victim: Greg, another 36-year-old business owner, but this time in the beverage industry — blond, nice and extremely well-meaning, but entirely off-putting. Second-date-able?: Not so much. He started most of his sentences with “If we should date…,” seemed generations too old for me and the chemistry was roughly -325, if such a scale should exist. Give him a chance?: He assured me it was fine that he paid for meal (it was a business expense after all) and… and… well, I’m struggling to pull another positive adjective out of the wreckage of the date, to be honest. Let’s just say I politely sped up the date as fast as I could and exited gracefully as soon as the valet pulled up.

And last, but certainly not least: This one is exciting, right? She’s got a little spark going here and things may be looking up for Date #2 with Handsome Man #4. We close in on a beautiful Saturday night in Minneapolis, scrumptiously ripe for the picking. The gentleman: Brandon, of monster-truck fame, comfortable in a t-shirt and jeans and making the trek from Rosemount to South Minneapolis in said monster truck, which, yes, looks strikingly similar to the image I selected for his post, but think more red. Excitement, fun and possibilities: After abandoning a ill-fated attempt to take in the Pizza Luce block party, we sauntered over to Cafeteria for beers and French fries. We laughed and talked about anything and everything. He called me judgmental (I deserved it) and I told him to stop using the word “ain’t” (because it ain’t a word). I revisited my college youth as we headed to Williams for a nightcap. Although everyone there looked ready to head back to Calculus 201 in the fall, we roosted on the bar stools and drank beer out of over-sized glasses. And — I promise I will always be honest, dear readers — I kissed him. Right smack-dab on the mouth in the middle of a dirty and crowded bar. It was sweet, innocent and absolutely set us on a path of it’s-not-going-anywhere, for who starts their “how we met” stories with a peck in the middle of strangers? The aftermath: Ever the lightweight, I was down and out (and ready for bed) sooner than any civilized 28-year-old adult should allow herself to be, and the night wound down from there. And wishing and hoping and praying (okay, that’s being slightly over-dramatic), I have heard nary a word in 2.17 days.

So… exhausted from eight or so meet-and-greets in the last month, I am ironing, listening to Fitz and the Tantrums (download it now) and digging up the courage to post this intimate and oh-so-personal update for the world to see.

It’s an adventure, not a destination, right? Or… Hmm.

Five

Sunday night found me at Chianti Grill, awaiting the arrival of Aaron, a 34-year-old human of the male persuasion. He had totally stolen my move by deciding to arrive late so I was neurotically checking my phone and glancing (stealthily) sideways at every fellow who strolled into the restaurant.

Instead of meeting a psychologist who was a department head (as per my phone call with It’s Just Lunch earlier in the week), I met a psychologist who works for the Department of Corrections. You know, as in he spends his day at an honest-to-God, locked-down-with-handcuffs PRISON. Aaron was a nervous, portly, sweet man and the date was off to a rough start so naturally upon hearing about his occupation, I grasped onto this conversation topic as if for dear life. I prodded him with so many questions about the ol’ jailhouse that he was barely able to get in any questions about me, which of course was the point. As soon as he had lumbered into the bar, I instinctively knew the date wasn’t going anywhere and I was reticent to share any personal details with him. Don’t get me wrong — I was impeccably polite and patient, and my heart went out to him as he fiddled with his napkin, and broke a bit as he departed to go to the little boys’ room (his words).

Needless to say, I ordered a salad due to its quick prep time and as politely as possible wrapped up the date as quickly as possible. Although I was discouraged, it got me thinking… What really goes through our minds when we meet someone new? In the past month, I’ve been blessed with the opportunity to meet a handful of new men and within the first five seconds, I’ve slotted them into their respective “it’s just not going to happen” and “okay, there’s potential” bins. Is there any sense to this or am I a hopelessly superficial person prone to judging people solely on their outward appearance?

Seriously concerned about my possible lack of character, I turned to my book collection for an answer. I snagged my copy of Malcolm Gladwell’s “Blink” and began rereading a few sections.

Turns out, and I quote, “it is quite possible for people who have never before met us and who have spent only twenty minutes with us to come to a better understanding of who we are than people who have know us for years.”

I don’t think there is any substitute for a relationship carefully cultivated over the years with love and mutual respect, but there is something to the snap judgments we make when encountering someone new. First impressions are everything. (Or not… you really can argue both sides pretty effectively, but for now, I will take comfort in the fact that our intuitive awareness counts for something.)

I’m off to bed for some much-needed sleep to reclaim my trademark sarcasm for tomorrow’s date in Uptown. But first, a bit of dancing, some Pinot, a text to Brandon confirming our second date on Saturday (!!) and plenty of Lissie on the radio.

In the words of my dearest Cloud Cult, I love you all!

No. #2

Okay, he totally had potential. Andrew, a twentysomething who had just moved back to Minnesota after a few years on the road, was Date #2. After meeting with Patti, the Millionaire Matchmaker — also known as Gina from It’s Just Lunch — and further honing my (our) idea of the perfect man for me, I was excited for the next dude on the list. Andrew owned two companies, was exploring his pilot’s license and lived for the outdoors. He was looking for an intellectual woman with whom to settle down.

After another sweltering performance of getting ready in my god-forsaken furnace of an apartment, I tumbled into Urban Eatery. Literally. Shoes slipping every which way. I was desperately trying to regain my balance while approaching Mr. Guy — he who had chosen the humid Amazon on which to perch instead of the air-conditioned heaven of a leather indoor booth — when I descended upon Sk8ter Boi 2011.

Andrew, a world-renowned ROBOTICIST (I’m not kidding) stared me down with the sort of charm one might expect a six-year-old to exude. He had gone to college at the age of 14 and in the past fifteen years, had built himself into a sought-after mechanical roboticist. Discovery Channel was finalizing a reality series with him and he had just closed a deal with Chrystler the Friday before. Despite the desperately-needed haircut and wardrobe retool, he was gregarious, open, passionate and up for anything. Including miniature golf and root beer floats.

Teetering in my black pumps and slinky (and severely discounted) BCBG mini dress, I had to steer the conversation back towards mutual topics, hoping to avoid a night at Lava Links. We chatted about Minnesota (gotta love the people), the weather (isn’t it crazy?) and the lakes (totally beautiful and great for paddle-boarding).

The highlight of my evening, I must confess, was our waiter. He turned out to be my first love. We were, no joke, fifth-grade sweethearts and had skated the snowball together to the delight of the rest of our class a few decades ago. We had a blast catching up on his marriage, studies and job.

I headed home for edamame, the new Bon Iver CD and some apartmental organization, satisfied with another great experience – even if the chemistry wasn’t there.

Dear Andrew, may you find your motorcycle-loving, seat-of-her-pants lady chic! Dear me, isn’t this fun? Next up… former band member and MBA-toting Karl, and Mike, the smartie baseball-playing friend of a friend.

Cheers!

Option #1

Last week, I took the inaugural step into the dating world on my first official date. Naturally, I was nervous while curling my hair into a messy wave and running around the apartment collecting the necessary odds and ends for my handed-down-with-love-from-grandma vintage purse. I hadn’t gone on a tried-and-true date in approximately 10.7 years. For realsies. Granted, I’ve had serious relationships since then, but none of the nature that started off with a “Hi, I’m Jenny – you must be…” handshake. Gina, my designated matchmaker, had set me up with Mike. Mike, the cute VP banker who loves sports and is looking for a kind, yet motivated, woman. After plunking down a hefty load of cash for It’s Just Lunch’s top-shelf service, I had high expectations.

I strolled into Barrio on Friday in high fashion. My much more aesthetically gifted friends had loaded me up with a brand-spankin’-new dress and I was feeling confident despite the sheen one naturally bared if one loved in a non-air-conditioned apartment during the summer that Minnesota literally melted.

Mike, a short, dirty-blond boy decked out in a branded golf shirt and ironed khakis, and I were seated. He was slightly divergent from what I had conjured up in my mind. Although very sweet (one might say timid), the VP title hid the fact that he was a true small town, country-music-loving farmer’s son. I scrounged up the image of me, living in a checkered two-story in Jordan, MN, whiling away the time to the latest Rascall Flatts album, and politely had to decline.

Before you judge me on my hastiness, know that I sat there, picking at the guacamole and sipping a way-strong margarita (okay, two seriously strong margs) for two hours. We chatted, I asked prodding questions like, “what most defines you” and “why the heck don’t you recycle, country boy” and we truly parted on good terms. He was shy, extremely good-natured and a perfect fit for an unassuming lady looking for a small town family and a dedicated husband. May he find that woman!

Undaunted, I headed home and watched a rerun of “Parks and Rec” before retiring to bed, book in hand.

Up next… Andrew.