20 is… plenty?

Sometimes you meet someone who satisfies a significantly decent portion of your dating criteria… Meet Joe Black, a 37-year-old entrepreneur from Winona, Minnesota. (Confession: I don’t know his actual last name, which isn’t shared as part of the It’s Just Lunch process, but it seems to fit so let’s just go with it. Also, not to confuse the reader, but my Joe Black has black hair, which is distinctly, and not unfortunately, different from Brad Pitt’s delicately golden, wispy 90’s highlights.)

Joe and I met at the newly opened Pittsburgh Blue in the Galleria. Our reservations weren’t until 8:00 p.m. so I had plenty of time to wrap up the work week, stop at Marshall’s for new workout pants and carefully paint on weekend-appropriate date make-up, which is essentially a lot of Bare Escentuals strategically applied to look like a little bit of make-up. Feeling the need to dress more formally for such a fine establishment, I slithered into my thank-God-I-just-dry-cleaned-these black tuxedo pants, pulled over a slightly sequined Banana top and popped my toes into my favorite pair of red pumps. Grabbing a fitted jacket, I was down the stairs and out the door with time to spare, and steered my trusty, non-gas-guzzlin’ Honda towards the Southdale area.

The date started out on the wrong foot. I had arrived and been seated before Joe arrived, and so when he slid into the booth shortly thereafter, I naturally began with “You made it!” and then spent the next five minutes explaining that no, he indeed wasn’t late, I was just early, and really it’s no big deal because, hey, I’m late ALL of the time. Awkward. (I’m also not sure he heard a word that I said, I was talking so fast.)

Joe was tall, dark and handsome. Well, two steps down from handsome, but still a good looker with a smattering of silver hair at the temples, which made him look distinguished rather than old. As we inspected the drink menu, I put my other foot in my mouth by sharing that obviously I don’t drink white wine (I mean, come on) and, since that was in fact all he drank, we settled on a Grey Goose gin-and-tonic for him and a Malbec for me. (P-Blue is spendy so I had to go with the cheapest red on the menu — classy!) Conversation eventually drifted towards fitness and the gym. Joe used to run several clubs and was a dedicated athlete — he ran, lifted and swore by yoga and kettlebells — and a bit of a health nut who loved his juicer. I didn’t have much to add to the conversation except a quip about the hydrating powers of coconut water and sat there in hopefully strategic positions designed to camoflage what I shall refer to as my “date weight.”

Our doting waiter shared the night’s specials and I selected the salmon (because it’s better for the world than red meat — Joe didn’t agree) and he elected for the steak because, well, it’s a steakhouse. The food was sumptuous and we turned the chatter to our professional lives. Joe was an entrepreneur in the strictest sense. He thrived on taking an idea and building it into a successful business, regardless of industry or trade, and had managed to secure quite the nest egg for himself. He worked when he wanted to, just moved into an apartment approximately five times larger than my 600-foot space (no exaggeration — he shared the square footage) and pretty much lived a fine life as a single, independent, well-heeled thirtysomething man.

In fact, after poking around a bit, I wasn’t sure if there was even room for somebody else in his larger-than-life world. He didn’t seem especially interested in asking any questions about me and when he did, it felt like a competition. Also, we weren’t laughing — just talking. And that’s huge. In my opinion, if you aren’t laughing on a first date, it’s not going anywhere. Life is long, our skin sags, friends disappear, money runs short, unfortunate things happen — if the person next to you isn’t there to laugh through it all once the tears are brushed away, what do you have?

So there I sat, spooning deliciously creamy butternut squash onto my plate and trying to make this into a great date. He was far better than any of the other guys I’ve met since July and technically I should be interested, right?

I have Joe’s business card and it’s been sitting on my dining room table for a solid week, collecting dust and slowly being overtaken by junk mail. When it catches my eye, I keep thinking I should send Mr. Joe Black a text (I’m too lame to actually call), but feel like I would just be forcing myself to do so. I wish had more to say, but that’s really it — I just never felt the urge to pick up the phone.

But here’s the thing — and I truly believe this — no one ends up with Mr. Perfect. We end up with Mr. Right. The one who failed our endless checklists, but still stole our heart.

14: The Over-Qualified Bachelor

His profile at the sperm bank would certainly be popular: A soft-spoken Hispanic gentleman who is an experienced surgeon, successful businessman, world traveler, volunteer and community leader; he’s been described as wealthy, attractive, well-dressed, highly athletic, cultured, knowledgeable, kind-hearted and in possession of a great hairline. Great genes, I daresay!

Luis and I met for dinner and drinks at Murray’s last Friday. I arrived ever-so-classily and on time (!!!) via car service, a sweet tip from a dear friend who knows my inability to be punctual and carry cash for parking. Luis was waiting in the bar and walked me to my table, whereupon a waiter bequeathed us with an extensive wine list. Over sips of a Pinot as smooth of silk, we decided on our own version of surf and turf — sirloin steak and a lobster tail that was essentially the size of my head. In steady measures of brief sentences, Luis shared an abbreviated summary of his life story — born in Central America to an affluent family, he had the choice to play on the national soccer team or head to med school. He trudged his way along the narrow path before ending up in the U.S. for his residency after being attacked and kidnapped for driving a flashy, fancy car. Over the next two decades, he settled into Midwestern life and worked his way up to the head position in a prominent surgical unit while acquiring another advanced degree here, a business there. You know, normal stuff.

Although my life story was clearly vanilla compared to his rocky road (I’m talking off-brand, yellowish, gallon-sized vanilla ice cream — not even of the Sebastian Joe’s variety), he was incredibly gracious and complimentary, and picked up the half-my-month’s-salary check. Being the chicken that I apparently am, I did accept his invitation for a second date. Although I was having a good time, I realized it was only because it was interesting, not because I was interested in him — and I politely rescinded via text message the next day like a true Gen Y lady.

I thus present why Date #2 with Bachelor #14 will not take place, which shall henceforth be known as Jenny’s Reasons Why Not. My argument is two-fold and structured as follows:

  • He is 39. There are 5,781,600 minutes between us. Luis is worried about hitting the big 4-0 and walking down the hill. At 28, I’m practically brand-spankin’ new. Heck, my lil’ sis just graduated from college and I still bring my laundry to my parents’ place (okay, maybe not the shiniest of points to make, but I’ll stand by it…). MTV was already two years old by the time my mom got around to popping me out. Luis surely will not be able to relate to my early teenage years, of which the better part were spent dreaming about the middle Hanson brother, reading The Babysitters’ Club and watching Bill Nye the Science Guy. (Man, I was a lame kid.) A wholly-unqualified elementary scientific approach to my self-described ageism is as follows:

  • He lives in North Dakota. Now, before my Fargo and Bismark friends start squawking, please note that this is a simple case of logistics. His practice is firmly stationed in the northernmost Dakota, while my heart remains in Minnie. Even if the date showed signs of promise, this would be a deal-breaker.

It was a fantastic night that knocked me slightly off-center if only as an exercise in reemphasizing what is important to me. Not the lifestyle, wealth or flash… just the guy who will love me in sweatpants, stop me from eating a full bag of Baked Lays in one sitting and gently remind me that I am never again allowed to rent an apartment without a dishwasher.

And, so, I head in a slightly different direction, carefully removing the training wheels that have padded my journey so far. If It’s Just Lunch is bowling with bumpers for dating, it’s time to remove said safety measures and take yet another chance. This time, I’m picking the guy, I’m defining the parameters, I’m in control.

This time, I’m meeting who I want to meet.

Well, That was Different… Moving into Double Digits with Date #10

Hmm. This one was a head scratcher…

A Thursday night date is always tricky. If you are anything like me, you are always trying to squeeze one more thing into your workday before you head out for the night. After a crazy day of scuttling around the office like a busy worker bee (and loving it), I finally glanced at the clock and realized I was in trouble. I flew down the stairs to the women’s lockerroom and hurriedly slipped into my #lifesaver non-wrinkle dress. A quick glance at my cell phone revealed how far behind schedule I was. It was either curl my hair or get my booty to the restaurant to make it on time. Naturally, I chose the latter. (Just kidding — of course I stayed behind to curl my hair. Obviously.)

Jeremy and I met at Collette in Bloomie. Fortunately, we were both running late when I showed up breathless and wreaking of Aveda Air Control and Escada Moonflower. We were whisked to our table and after a few minutes of “I’m so sorry I’m late” and “I need to spit out my gum – where’s some paper?” conversation, he hit me with the big question. So, why, exactly, are you paying for this service? He spoke from a position of resentment so I turned the question back on him, feeling he likely had something he needed to air. Turns out, this was his absolute last It’s Just Lunch date. Overall, Jeremy had not enjoyed his previous 14 dates and was calling it quits-to-bits. Meeting the IJL ladies wasn’t any fun and felt like work versus entertainment. He hadn’t met the caliber of mademoiselle he had hoped for. Fair enough. Listening to him, however, I felt fortunate that although I hadn’t yet met Mr. Perfect Amazing Stud Man 2011, I was still enjoying my mis-matched dates for what they are — a chance to share a moment with someone who could shape your life forever or for the next five minutes. That’s worth something.

Firstly, Jeremy had a six-year-old son, which is — cringe — sort of a total deal breaker for me. Sorry. Secondly, Jeremy, real estate extraordinaire, was rolling in the dough and not afraid to declare it. He had thrown down so many dollar figures within the first five minutes of meeting me that I was struggling to keep up. Spouting off your accomplishments in numeral form is probably one of the least attractive things a man can do on a date. Surely, your priorities are not in the right place. Yet, he kept going, keeping up a steady diatribe of angst against the institution of professional dating.

It was weird. Although the lines had been drawn — no second date would surely take place — we kept chatting. I hadn’t met anyone who was diametrically opposed to me before he had even met me, and I found the conversation was keeping me on my toes. My randomness irked him, my off-the-wall hand gestures annoyed him and my snarky comments simply fell flat. I hadn’t been on a date that honest in a long time and it was refreshing. Although, please read above, this was clearly going nowhere.

We didn’t exchange numbers or pretend to be interested in more and this stick-to-reality approach was interesting. Onwards and upwards, my friends.

Next up — Brent. Then Luis, my mini Millionaire Matchmaker man.

Cheers!

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.