#reasonswhyimsingle: Princess and the Pee

The “Hot Mess”.  

We all know that guy who takes fun to a whole new level, partying twice as hard as his age should allow, and continually reeling in people who, like myself, have a chronic case of FOMO.  There’s at least one in every group of friends, and during a monstrous lapse in judgement, I just happened to fall for one.  (Now keep in mind this was years ago and I will continue to stand by the excuse that I was drunk the entire time we hung out).

In all seriousness, though, Mr. Hot Mess isn’t a bad guy…when he’s sober.  He’s the lovable comic relief that seems to come around just when life is getting too serious.  He’s the life of the party (the first half, anyway) and the source of endless stories, each more hilarious than the last.  He’s also notorious for being a “Redeemer,” one of those people you just can’t, in spite of yourself, stay mad at for very long.

Mr. Mess and I have known each other long enough (and have been through enough shenanigans) that when my friends say his name, it’s usually accompanied by an eye roll and a long, judgmental groan.  I always know they have my best interest in mind, and I also knew it was going to take something pretty major for me to lose that soft spot I had developed for him over the last few years.

Sure enough, that day came a few months ago.  I was out to dinner and he called me to report that he was in town, drinking at a bar that was conveniently en route back to my apartment.  As usual, my irrational fear of missing out on fun got the best of me, and I soon found myself in a crowded college bar.  Despite being the oldest human there, I was downing shots of Fireball in between rounds of 90’s karaoke.  I’m more than a little embarrassed to say that I was having a total blast.  But I did kill some Salt ‘N Pepa that night, so there’s that.

We met up with some friends, including my roommate at the time and the guy she was dating.  As the night flew by, Mr. Mess became more affectionate – and less articulate – and soon all of us were cramming into a cab to head home.  We sat around drinking beers (unnecessarily) in our living room, which was scattered with boxes of my things in preparation for my upcoming move.  In order to avoid last-minute stress, I had been slowly packing items that weren’t in use.  In my bedroom were several boxes of kitchen appliances and a bright green binder where I had organized and filed all my important documents.  I would soon come to regret being proactive, but I digress.

Fast forward a few blurry hours later when we all decided to go to sleep.  And by sleep, I actually mean it. In his drunken stupor, Mr. Mess had inadvertently blurted out that he had a new girlfriend, abruptly putting an end to any flirting that was going on between us.  Despite his best efforts to back pedal, he quickly resigned to the fact that he would be spending the night on the couch.  (Admittedly, I don’t make the best of choices at times, but fooling around with men who are spoken for is not one of them).

Anyway, back to when I was sleeping.  And soundly, might I add, which is why I was shocked when I became increasingly cognizant of a low, faint noise.  At first it sounded like rain falling onto a cloth umbrella and soon grew to a loud noise that I somehow recognized instantly.  I shot up in bed, screaming for him to stop.

The sound I was hearing was a stream of PEE hitting a cardboard box, the same one I had packed my kitchen appliances in.

I grabbed Mr. Mess by the shoulders, yelling, and shook him until he awoke enough to realize what was happening.  He was groggy and stumbling, and I shoved him out of my bedroom.  Furious, I continued yelling at him as he walked right into my roommate’s bedroom.  At that point, I forfeited all regard for my sleeping roommate (sorry) and directed him to the bathroom, shouting the whole way.  I stormed back to my room and slammed the door, making sure it was locked this time.

I was too exhausted and pissed (ha) to even turn on the lights and deal with the mess he’d made.  I quickly surveyed the damage, brought my blender to the kitchen to pour out the urine that had collected, and collapsed back into my bed.

The next morning (AKA three hours later), I reluctantly pulled myself out of bed and glanced around the room.  In the morning sunlight, I realized that he had not only peed into my box of kitchenware, but also into my work bag..and ALL OVER that bright green binder that held everything from tax returns to my birth certificate.

Now let me ask you this: What on earth do you do with documents soaked in urine?  Wash them? Throw them out?  Make him bring my social security card downtown and explain why I needed a new one?

Besides my hangover, the worst part was that he had no idea.  I had to explain the entire ordeal to him, in detail.  He shamefully sat on the couch and my roommate stifled bouts of laughter while I berated him like a child.  I did feel a little bad after I realized he was completely (and understandably) humiliated, and he offered to replace everything in order to fix what he’d ruined.  Through clenched teeth, I calmly explained that most of the things he peed on were un-fixable.

After brainstorming for a bit, it seemed the only option was to carefully separate the papers, lay them out around the house, and let them air-dry.  

(Side note: If anyone has a better solution, please feel free to comment below…Pinterest wasn’t very helpful).  

Mr. Hot Mess offered to buy the blender, which I happily agreed to since I couldn’t bear the thought of making pee-smoothies every morning, and he apologized profusely before grabbing a cab home.  

While I can laugh about it now, (the thought of him doing the walk of shame with a blender under his arm never gets old), I was exasperated at the time.  

Soon after he left, the cleaning lady arrived at our apartment.  I had completely forgotten she was coming that day, and I told her to skip my bedroom in fear she might realize what she was cleaning and never come back.  As she was cleaning the bathroom, however, she unassumingly brought out the rug, asking why it was soaking wet.  My roomate and I looked at each other, wide-eyed, and quickly told her to just put it aside.  How was that much pee even possible?  We made sure to giver her an extra-big tip that day.

If nothing else, that morning made me realize that I’m just too old for this.  

Isn’t there a saying about people coming into your life for a reason, a season, or a lifetime?  For me, it’d become glaringly obvious that the season of “Mr. Hot Mess” had abruptly come to an end.

Sure, my friends laughed hysterically when I told them later that night, but I knew it would be the last ridiculous story I’d be telling about that man.  We haven’t spoken since, and although I’m going to miss some of those great, fun times, I’d much prefer my life to be mess- and pee – free.

Lesson #6:  Urine charge of who you associate with.  Don’t mess it up.




#reasonswhyimsingle: How I Met His Mother

After taking a several-month hiatus from online dating this winter to re-kindle an old flame (seemed like a good idea at the time), I found myself back in the game this spring, just in time for March Man-ness.  

I chatted with an attorney whom we’ll call Matt*.  He was bright, witty, and had an adorable picture of his dog, which I’m a total sucker for.  He, too, seemed like a good idea at the time.  

Fair warning: this story’s a little long, but I just have that many awful details to share.

Of note, I was also talking to a guy named Jim* whom I’d met at my favorite bar a few months back.  Even though he was nice, he was one of those guys I like to describe as “vanilla”.  Just like the ice cream, he was normal and well-liked…but nothing special or exciting.  We’ll get to him later.

Back to Matt.  On this particular night, we agreed to meet for drinks around 9pm.  When I got out of work earlier than expected, I sent him a text asking if he wanted to move up the time (because I’m old), and he happily obliged.  He was already at a bar with some co-workers watching the first round of March Madness so I agreed to meet him there for some beers & basketball.  Since it was (supposed to be) a casual date, I dressed accordingly and headed off to meet him.

He was waiting alone at the bar wearing glasses and a suit, drinking what looked like scotch (how cliche), and he greeted me with a huge smile and a big hug.  He wasn’t quite as cute as I’d hoped, but he did have a seat saved and an ice-cold Allagash White waiting for me.  I’ve learned that any guy who pays attention to what you like to drink-and has one waiting-always deserves a few extra points.

Our conversation started with some casual talk about our brackets and lead into the usual discussion about jobs, neighborhoods, and favorite hang-outs.  He told me about his family and for a guy whose roots were steeped in old-money Chicago, he was humbly aware of his privilege and spent a lot of time volunteering in under-served communities on the South Side.  More bonus points.

The date, however, began to head to the South Side when I asked him about that adorable dog in his photo.  He told me all about his pup before adding, “I actually boarded him tonight, which I hate to do, but I wanted to be able to spend plenty of time with you.”

How long do you think this date is going to last that you felt the need to KENNEL your dog?!?!

I ignored his presumptuous comment and changed the subject, and as we continued our conversation he asked me if I wanted to grab some food.  

My inner chubby girl responded “Sure, want me to ask the bartender for menus?”

“Wellll”, he said, “I actually made dinner reservations down the street for us.”

I was a little taken aback (I mean, when did he make reservations, when I was in the bathroom?).  I hesitantly agreed.  

We walked down the street to a fancy French restaurant ($$$$ on Yelp!) and I felt completely out of place in my jeans.  How we went from basketball to bourgeois is beyond me.

We were seated at a dark booth and he slid in next to me on the same side.  Who does that on a first date? 

It was at this point when I realized I should have declined dinner, but I was now, quite literally, trapped.

The waitress came over and we ordered both drinks and dinner (I suggested ordering right away to expedite this increasingly uncomfortable experience).  I don’t think I’ve ever eaten a steak so quickly in my life, which is unfortunate because it was nothing short of an amazing meal.  Except for the fact that Matt kept touching my arm and trying to hold my hand (That’s my fork hand, bro!). After we finished eating, he put his arm around me and I instinctually pulled away (probably my body telling me to get out…and fast).  He laughed, trying to pull me closer, and I was resisting so strongly that his fingers were digging into my neck.  He teased, “Oh come on, you know you like me.” 

I glared at him and sternly replied, “I haven’t yet decided whether or not I like you,” (I didn’t) “but I have to use the restroom.”  

In the bathroom, I thought about how to plan my escape.  I checked my phone, and Jim had sent me a text saying he was at a concert nearby and asked me to join.  YES! I desperately needed a change of scenery, even though it was now long past my bedtime.  Instead of ducking out without saying goodbye, I decided to politely return to the table to wrap things up with Mr. Handsy.

My date was walking toward the restrooms when I walked out, and when he returned to our table, he asked, “So how much do you like me? …Because my parents are here.”


There are THREE MILLION people in this city.  How in the hell did we just “happen” to be at the same restaurant as his parents?

He quickly saw that I was NOT into the idea of meeting them,  and he fumbled with his words, explaining that he had no idea his father’s company was being honored at an awards ceremony that night.  At this exact location.  Seven thousand restaurants and they were in the room directly behind us.

I frantically asked him to get the check so I could pay my half and leave.  Truly, I was willing to buy the entire menu just to be done with this date, but he insisted on paying.  He then insisted on sharing a cab, and I was quick to point out that he lived in the complete opposite direction.

“That’s ok, I’m happy to ride with you up north to drop you off at home.”

Ummm, no.  First off, I didn’t want this creeper knowing where I live.  Also, I wasn’t going home.  I pulled up Uber and yelled, “Already got a cab!” 


I had 2 minutes to kill before my life-saver arrived, and I just had to ask: “When exactly did you make these reservations, anyway?”

“Honestly?,” he said, “I watched you walk into the bar and thought you were so beautiful that I knew I didn’t  want to just have drinks with you.” 


They say the difference between a creepy guy and a romantic one is based soley on how attracted you are to him.  In this case, he made my skin crawl.

Just as my cab pulled up, his parents walked out.  And waved to us.  Not one to be rude, I waved back, hurled myself in the cab, and sped off to meet Jim.  

This one really takes the cake but as always, I try to look at the positive.  When I saw Jim that evening, it was in a new light.  I gave him a giant hug, relieved to see the familiar face of someone normal

In the long-run, I knew Jim and I wouldn’t last, but in that moment, plain old vanilla was exactly what I needed.

Lesson #5: Don’t ever let your inner chubby girl get the best of you…drinks, just stick to drinks.


*name has been changed…or has it?


#reasonswhyimsingle: Benefit of the Doubt Date

Benefit of the Doubt:
Noun. A favorable judgement given in the absence of full evidence.
See also: Wishful Thinking

Two years ago, I went through a phase, albeit brief, where I tried to think outside the box…as in, go out with guys I normally would never consider as a potential match. I had gone on a string of terrible dates and thought I might have better luck changing up my MO. Logically, this was justified: sticking to my “type” obviously wasn’t working for me. Truth be told, I was also on a mission to prove to my family that I am not, in fact, just too picky. (We can talk about how much I despise this phrase at a later time).

Anyway, I decided to keep the basic requirements in my search for true love (educated, employed, non-murderer), and let go of any expectations which may otherwise deem me too picky.

So what did I end up with?


Victor was a 30-something finance guy who seemed awkward, nerdy, and genuinely nice. He was smart, way too successful for his age, and not terrible-looking, so I went for it. Plus he asked me out about twelve times (ok, it was three) before I said yes. To be fair, he kept wanting to meet for dinner on Saturdays, which are strictly reserved for friends, beer, and college football. Pro Tip: Precious weekend nights are not to be wasted on first dates, let alone online ones.

But I respected his persistence and agreed to meet him for dinner after receiving the following text:

“Let me take you out to dinner Saturday. I know a great place in Wicker Park & I think you’ll love it.”

I was breaking my “No First Dates on Weekends” Rule in hopes that this nerdy finance guy would turn out to be wonderful. From what I knew of him so far, he wasn’t my style at all: serious, un-athletic, and he wasn’t very keen on sarcasm, which is kind of my thing.

But I gave him the benefit of the doubt.

Saturday came, I told my friends to save me a seat at our usual watering hole, and I headed to the restaurant. I walked in and saw Victor sitting at the bar, finishing his beer. He seemed really nervous to meet me, and we quickly hugged before asking the hostess for a table.

And that’s precisely when things went downhill.

Now, to fully convey just how mortifying my life was for the next hour and a half, I need to explain the layout of our surroundings: The restaurant was dark and quiet, made up of two rows of (very) small tables that were lined up so closely you could pretty much eat off your neighbor’s plate…or overhear a ridiculous first-date conversation, hypothetically.

There were two married couples on either side of us, and I’m fairly certain they stifled bouts of laughter each time Victor shouted something ridiculously awkward across the table:

“So I read your profile, but tell me more about yourself!”

“What are the top three things you like about living in Chicago?!”

My eyes darted from side to side.
Shut up, Victor! People can hear you!

If that damn table wasn’t so small, I would’ve crawled underneath it.

But in my head, I could hear my Mom’s kind voice, telling me to be nice. He was, after all, trying really hard, and it was clear he had prepared these questions ahead of time:

“So if you had to choose an animal that describes you, what would it be?”

“What super power would you most like to have and why?”

“Name three things you don’t like about living in the city.”

Finally! A question I knew the answer to! Ummm, dating in general, this tiny-ass table, and you.

But I held my tongue, politely answering his questions and putting forth a genuine effort to try to like something, anything, about him. I failed miserably.

I couldn’t wait for it to end. The food was served tapas-style, so we had to awkwardly share each plate, and I let Victor do most of the ordering since I hadn’t heard of half the things on the menu anyway. I picked at my dinner, wondering what on earth he’d ordered. Beef tongue risotto? At one point our conversation literally went like this:

(Both silently chewing)
Victor: Sooo, what’s your last name?
Me: Uhh, Lawrence.
Victor: Hmmm, ok.
(Both go back to chewing)

Please make it stop.

I could’ve hugged the waitress when she brought our check at the end of the meal. It was done. I had survived the most uncomfortable date of my life. And then Victor sat there with the check at his side for what seemed like eternity, continuing with his terrible questions. Did he google “First Date Conversation-Starters”? Why aren’t these married people saving me? In my mind they were my allies, sympathizing with me as I struggled to smile and nod.

Finally, there was a long pause in the conversation and Victor picked up the check, asking, “Ready to settle up our tab?”

WHAT? I hesitantly reached for my purse.

Don’t get me wrong, I’m all for splitting the check on first dates…sometimes. But this guy asked me, repeatedly, if he could take me out to dinner. And then he suggested this stupid place with their fancy menu and pretentious tables. I sighed and took the check from him.

Sixty-five dollars. Each. Before tip.

And I was still starving.

I put down my debit card and Victor asked the waitress to split the tab. He then asked if he could add his valet charge to the bill. The waitress awkwardly told him that, no, the valet is separate and needs to be paid in cash. Which apparently he didn’t have because he then asked her if he could give her an extra $10 in her tip in order to get cash back.

I was mortified.

She told him no, and that he’d need to use the ATM down the street. I had completely run out of patience, and practically shouted at him that I needed to leave in order to meet my friends.

Without so much as a hug goodbye, I quickly thanked him (for what?) and ducked out the door.

As I walked away, I glanced into the window just in time to catch the gaze of my married allies, still sitting at their tables. If nothing else, I hoped the stark reality of awful dates made them more appreciative of their spouses. Or maybe they just laughed at me. Regardless, I grabbed a cab and headed toward my friends feeling defeated. I try to stay positive and find humor in my experiences, but for some reason this date really got to me. I guess that’s what I get for lowering my standards.

Lesson #4: Don’t be afraid to aim for what you want. There’s no shame in being picky.

*name has not been changed because I really hope he reads this someday. And learns what taking a woman to dinner really means.



#reasonswhyimsingle: I Wear My Heart (and My Dinner) on My Sleeve

I’m clumsy.  So much so that my Mom put me in t-ball instead of dance class at the age of 4 because she knew I’d never fit in with those girls who were blessed with grace and femininity.  Needless to say, almost 28 years later I’m no more graceful – and only slightly better at softball – than I was as a child.  This tends to foster unfortunate, yet hilarious, challenges to dating.

Remember in my first post how I mentioned that I take full accountability for many of my dating mishaps?  Well this is one of those: my clumsiest date of all time which resulted, ironically, in one of the more successful relationships I’ve had in a while.   My date later told me that he found me endearing.  At the time, I was beyond mortified…and shocked when he kissed me that night and asked when he could see me again.

His name was Kevin*, and we met last summer after exchanging a few emails back and forth.  For our first date, Kevin and I met for coffee and ended up heading to the bar next door when the coffee shop closed.  We both had other obligations that night so we had a quick beer and he asked if he could take me to dinner the following weekend.  It was one of those rare, really good first dates, so I happily agreed.

Unfortunately, I’ve found that the extent to which I like a guy is directly proportional to how awkward I am around him, so the following weekend before he picked me up, I pre-gamed a little to calm my nerves.  We went to a restaurant in my neighborhood that I was dying to try: great food, a long wine list, and an outdoor garden patio with a fountain.  It was adorable.  And the perfect setting for the romantic summer evening date that I had planned in my mind.

We sat down at a small wooden picnic table and ordered drinks.  The sun was starting to set and it was a beautiful breezy summer evening.  We chatted for a bit about our week, and I felt really comfortable around him.  He was kind, funny, and genuinely interested in learning more about me, a trait I have come to find exceedingly rare.  My romantic evening was going perfectly…for about about four and a half minutes.

Exactly two sips into our drinks, Kevin was asking me about my job, which I happen to love.  Quite possibly too much, because I get really into it when asked.  While passionately telling him about being a nurse, my hands gesturing flamboyantly, I knocked over my glass – spilling ice and vodka all over our adorable picnic table.  We both paused as my drink dripped through the slats onto my feet, and I giggled awkwardly, apologizing as I called the waitress over to ask for napkins.  Whoops.

Kevin couldn’t have been nicer about it.  He cleaned up my mess and ordered me another drink – all without judgement.  We went back to our conversation as if nothing happened, and I was impressed that he didn’t seem fazed at all.

After looking over the menu, he was agreeable to my suggestion of doing a “half & half” for dinner.  (For those of you whose lives do not revolve around food, a half & half is when you each order an entrée and then split both).  The best of both worlds.  I usually reserve this suggestion until the third date or so, but he seemed cool and the decision of scallops vs. smoked meat was torturing me.

When the food came, we sat side-by-side, eating our feast and laughing about pretty much everything.  I was having a great time until I reached over for a scallop and it fell off the fork before it got to my mouth.  Trying to be nonchalant, I casually wiped it off the table with my napkin.  Such a waste.  But Kevin didn’t seem to notice so we continued on with dinner until I did it again.  This time with couscous, spilling little grains onto the table and my lap.  What is happening to my perfect romantic evening?!

I decided it would probably be best for both of us if I stopped eating, so Kevin finished off our half & half and we had another cocktail after our plates had been cleared.  It was dark, and candles flickered on the tables as we sat listening to the fountain.  It was perfect.  Just a few spilled items, but no biggie.  Kevin must not have noticed – or didn’t care – because he never said anything…

…until I gleaked on the table.   I don’t really know how it happened but he must’ve said something funny because I laughed, and SPIT on the table.  Gross.  This would have been a non-issue in front of my friends, but this poor guy had just met me.

He laughed, teasing me, “Did you just gleak on the table?…like, right next to where your food fell off your fork?…like, right next to where you spilled your drink?”  He laughed again, and I realized he truly wasn’t judging me.  I started to laugh uncontrollably, and I’m sure everyone around us thought we were crazy.  But we didn’t care, it was hilarious – one of those laughs that makes you tear up and gasp for air at the same time, and we both just couldn’t stop.  Finally, I took a deep breath and Kevin looked at me, starting to laugh again, and said “Ummm, you should probably go to the bathroom and look at your face.”  I bolted into the restaurant and down the stairs toward the bathroom, and took one look in the mirror.  I had streams of black running down my cheeks and all of my makeup was smudged.   Get it together, Jennie!  What the hell is wrong with me?

I tried to fix my face before walking back to the table.  He was smiling, shaking his head.  “I see I’m going to have my hands full with you,” he teased.  You have no idea.  We finished up at the restaurant and headed to a bar down the road for a beer.  The rest of the night went smoothly, minus one small trip going up the stairs when we got to the bar.  Kevin was walking in front of me, so he didn’t notice.  Or did he?  Regardless, he walked me home and kissed me goodnight, asking when he could see me again.

I was pleasantly surprised.  He saw me at my most awkward and clumsy self, and liked me anyway.  I remember thinking that this could be something really good. Unfortunately, we broke up a few months later (which is another story in itself), but it was a great reminder that there are people out there who will like you in spite of all your quirks, even on the second date.

Lesson #3:  Own your quirks.  Just don’t introduce them all at once.  

*name has been slightly altered in case he ever reads this.



#reasonswhyimsingle: Bacon

It’s 11pm on a Friday night and I’m happy to report that I’m staying in for the evening…someone call Ripley’s.

Since I just started a new job, I’ve been working long hours and trying to soak up all the knowledge I can…leaving me physically & mentally exhausted by week’s end.

That being said, I’d been looking forward to this evening all day: the chance to relax and make dinner while sipping wine and listening to Norah Jones radio. Don’t judge.

My roommate had just flown back from vacation and, like the fabulous girl she is, was already rushing off to a date. She’d been casually seeing this guy that she met on her birthday a few weeks ago. In doing so, one of his friends and I began chatting one night and he asked for my number. I like to call this “secondary dating”.

Anyway, we hung out a couple times, nothing serious, and he ended up texting me tonight asking what my plans were for the evening. I downplayed my excitement for Norah and just told him I was laying low.

Shortly after my roommate left, I lit some candles and poured a glass of wine before realizing I was too exhausted to cook an actual meal. So I decided on one of my go-to’s: “breakfast dinner.” Plus I’d just bought these fresh organic eggs and was looking forward to trying them. #thingsyousayinyourthirties.

I whipped up some eggs alongside a hearty portion of my all-time favorite food: bacon. I was sitting on the couch with my breakfast and wine, scrolling through Netflix, when I heard a knock on the door. Who on earth could be interrupting my fabulous night alone?

It was my roommate’s date, who had apparently confused the plans and arrived at our apartment instead of meeting her at the restaurant. Not thinking, I welcomed him in from the cold and explained that she had left awhile ago to meet him. While he stood in the apartment calling her, I noticed his eyes darting around the room, carefully taking things in:

Netflix, music, candles, wine, and me by myself in pajamas and no bra. Oh, and a giant plate of fucking bacon on the table.

Why I answered that knock in the first place is beyond me. He quickly thanked me and ran out the door to grab a cab. And I’m sure he needed privacy to call his friend and tell him never to speak to me again.

Remember that time I said I was usually responsible for my dating mishaps? Well, lesson learned:

Lesson #2: Always look your best. You never know who (or who’s friend) is watching.

As for the rest of the night, I’ll be shamefully binge-watching Criminal Minds while I finish my organic eggs. And another bottle of wine.



#reasonswhyimsingle: The Vampire Diaries

As I mentioned in my first post, my first “online-dating date” was, well, a learning experience. But looking back I have to admit, it was one of the more refreshingly honest encounters I’d had in a while.  It was also one of the fastest dates I’ve ever gone on.

His name was Val (yes, like the girl’s name). He was 44, attractive, fit, and owned his own IT consulting firm. On paper, a great catch. A little beyond my age range but I didn’t put too much thought into it.

We talked for quite a while via email since I was hesitant to meet a stranger from the internet machine, let alone in the city of Chicago. I strategized what I would do should I find myself in a dark alley with a knife to my side. (In case you were wondering, faking a seizure won out as the best option in this scenario).

Armed with my foolproof rape-escape plan, I stood on the corner near the restaurant where we were meeting.  I watched people flood off the train and into the street, and I considered turning back to go home. Never one to back down from a challenge, I reminded myself that it was just dinner and drinks.  I love drinks!  I can do this!  Move, feet!

I saw Val in a booth and he stood up to give me the obligatory/awkward first hug. He looked just like his pictures which, of course, made me more nervous since he was actually hot in real life.  Thankfully, our martinis didn’t take long to arrive.  The conversation was nice at first, with the usual getting-to-know-you material, blah blah blah, and I started to remember how fun it is to meet someone new.  Especially a handsome someone new.

By the second round of cocktails, I was feeling pretty good about things, and proud of myself…for not being myself.  In my truest form, I can teeter on the edge of being one of the guys since I grew up being, well, one of the guys.  I blame my three brothers.  So, as all my friends know, I’m not very girly. BUT, I’m working on it.  Oh, and I’m terribly clumsy, but we’ll get to that another time.  Regardless, I was nailing it.

At this point, Val brought up my name, which people are always commenting on ever since The Hunger Games became a thing. Speaking of starvation, the waitress came by and I was eager to order some food, especially after gulping down two martinis. When I started to ask if he had a chance to look at the menu, he interrupted to tell our server that we were just getting drinks.  We were?  Damn.  I realized this was clearly a man on a mission.  Not that I was planning on eating a full meal in front of him (not true) but please don’t interrupt me and for God’s sake, offer a girl an appetizer.

So anyway, back to the name thing…and I bring this up because this is the point at which the night took a turn for the worse.  Our Hunger Games/Jennifer Lawrence banter quickly segued into a FIFTEEN MINUTE rant about how my generation “is simply OBSESSED with these stupid fictional movies and books.”

“And I don’t get why you kids are so into vampires!  What’s up with that?”  He went on and on, rivaling a grandfather’s speech about “kids these days.”  I quietly sipped my drink wondering if he was going to stroke out from all his fervent ranting.  I sat there grinning uncomfortably for a bit…until I just started getting mad.  This is not my grandfather, this is a guy that asked me out on a date, with full knowledge of my age in advance.  In my mind, I contemplated ridiculous ways I could respond:

A) Agree with him: “OMG. You are so right.  You should probably buy me another drink so we can discuss further.”

B) Point out the obvious flaw in his logic: “While I’m not a math expert, I am fairly certain you are (only?) 14 years older than I am.  I don’t think this constitutes an entire generation. But I could be wrong. You should probably buy me another drink so we can discuss further. Oh, and food.”

or C) Tell him what I was really thinking: “I didn’t even read Twilight, you dick.” 

In reality, I just interrupted and flat-out asked him why he would even want to date someone my age, given his strong opinions about us embryo-folk. His response?

“I want to have children.  Soon.  And I’m 44, for crying out loud. If I date women my own age, that will never happen.”

Yikes.  Note: He actually used the term “for crying out loud.” Shit was getting real. 

So I’m basically having dinner drinks with a man who has some deep-seeded concerns over someone else’s biological clock?  Hmmm.  Based on his earlier math, I guess I couldn’t blame him – he was at least two generations behind on making babies.  A part of me was surprisingly impressed with his blatant honesty, and for just a split second, I almost found him endearing.  Almost.  But you know what?  If the roles were reversed and I spouted out on a first date that I needed to find someone to have kids with, ASAP, there’s no man on this earth that would find that endearing…or even tolerable.  I made a mental note to stop justifying men for things that would otherwise label women crazy.   

Getting back to my story, I’m pretty sure crazy Val could tell by the terrified look on my face that we were not on the same page.  Or even reading the same book for that matter.  Not one to waste any time, especially with that ticking clock of his, he promtply asked for the check.  I was speechless.  Can I at least finish my drink?  My silence prompted him to apologize that our goals didn’t align, but he needed to be upfront about his expectations.  I respected the guy for knowing exactly what he wanted and not being afraid to ask for it, but God Bless. 

The night ended cordially, he wished me the best in my search, and he shook my hand.  Was I just on an interview for a job I didn’t even want?

Although I never saw him again, I imagine Val’s direct approach probably landed him exactly what he needed: a co-dependent 20-something who loves T-Swift, True Blood and – for crying out loud – babies.   

As for me, I already hated online dating.  But I couldn’t let one bad experience get me down.  Little did I know, this date would pale in comparison to the craziness of others.  At least I got a few (quick) drinks out of the deal, right?  Speaking of which, I failed to mention the icing on that evening’s cake:

When the check came, Val took the opportunity to take one final stab at my age: He grabbed his credit card and presumptuously remarked, “I got this one.  I’m sure you’re still paying off student loans.”


Nonetheless, I decided long ago to take something positive from every failed romantic encounter, so here’s what I learned:

Lesson #1: Be yourself. Even if you’re crazy. Eventually you’ll find someone who feels just as strongly about your beliefs…and vampires.



Jennie From The Blog: Intro to #reasonswhyimsingle

With the holidays quickly approaching, I’m looking forward to traveling to my small hometown to eat, drink, and be un-married. Despite well-intentioned enthusiasm, I find myself irrationally annoyed – and reaching for the wine – whenever one of my dear, sweet relatives feels the need to be my relationship cheerleader.  “Don’t worry! You’ll find someone! Rah! Rah! Sis boom bah!”


Since I cannot, with a good conscience, tell my elderly relatives that they all need to just calm the fuck down, I’ve devised a new plan: All questions and concerns surrounding my romantic relationships shall hereby be deferred to the blog.

Also, I’ve been looking for an excuse to write this for the last year so grab a glass box of wine and bear with me while I explain…

The idea for a dating blog came about two years ago, when I took the match.com plunge with my roommate Katie*.  I was about to turn 30, had finally established my career in Chicago, and I was ready to make an honest attempt at “putting myself out there,” whatever that meant.  Katie and I actually went on our first match.com dates on the same night, just a few blocks from each other.  I’m excited to report that Katie’s story went something like this:  Go on first date, fall in love, cancel match.com subscription, move in with boyfriend, get engaged, plan beautiful fall wedding.  Boom. Simple, straightforward, and uncomplicated.  HOW DOES THAT EVEN HAPPEN IN REAL LIFE?!  Truly, though, I couldn’t possibly be any happier for her.

Needless to say, my dating experiences over the last two years did not go quite as smoothly, but at least I have some hilarious stories to show for it. The best comparison I can come up with is this: You know how people who are bad at golf can at least joke about how they got their money’s worth for the round? Well, after my first “online-dating date” (which was bizarre in itself), each subsequent experience seemed more ridiculous than the last.  Soon my friends and I were sitting around drinking Franzia on a weekly basis, cracking jokes at the latest comedy show that was, in fact, my love life.  I always said I could write a book on bad dates, so here it is.  Now, it may or may not be true that I am, in fact, terrible at dating.  So I blame myself for some (well, most) of these, but here are just a few of my most hilarious, endearingly-awkward, and painfully honest stories of #reasonswhyimsingle.

*names have been changed, barely.