Valentine’s Day, the Perfect Date and Awkward Jean


I know, I know… It’s been awhile. Lo siento mi amigos. (I’m sorry my friends.) What can I say, I was busy/sick/uninspired/____(fill in the blank). BUT, rest assured the last six weeks I’ve been just as awkward as ever. Trust. What I haven’t been is focused on my whole endeavor of trying something new each month. Sorry about that, but I’m sure I’m not the only one with grand intentions that all too often unravel and fall short. However, today is the official first day of Spring and it brings with it a fresh start, new growth, yada yada– I’m sure you can see where I’m going with this. Bottom line — Awkward Jean, and all her misadventures, is BACK!

Now, as I mentioned, I have fallen very behind in my attempts to try new things and chronicle them here for you, what I haven’t disappointed you with is some awkward moments à la Jean. So, pour yourself a beverage of choice and get cozy while I tell you about the time I went bat-shit crazy thanks to the pressures of Valentine’s Day AND the time I went bat-shit crazy thanks to the pressures of a nearly perfect day with Crush.


It all started a few days before Valentine’s Day. A friend of mine has been having a few medical issues and had just learned from her doctor that she is pre-menopausal. This friend is only a few months older than me and, like me, doesn’t have children. She was married, is divorced now, and is suddenly faced with the fact that IF she even can have children she likely needs to do it in the next year. As she sat there sharing her initial reaction and fears and questions I found myself thinking that this could be me. She is my age. What if my doctor suddenly told me I had a year to make all my dreams come true, or to change my dreams. Suffice it to say I struggled to stay focused on her, supportive of what she may need — a shoulder, an ear, a bottle of wine — but as selfish as it is, my mind started going a million miles a minute about my life. Where I’m at. What I want. What I need. What I’d do. And then the horrible moment when I realize, this is my life. I am her. There is no guarantee. I am thirty five and this may be as good as it gets. 

It was with this distracted mind and heavy heart that I talked to Crush on the phone that night trying to focus on jovial and topical conversation. I tried to push all my scenarios and thoughts and fears and questions out of my head but instead what happened is mid-sentence I interrupted whatever Crush was saying and blurted out —-

Awkward Jean: DO YOU WANT TO HAVE KIDS? Er, I mean, not with me. Well, Not NOT with me, I mean maybe, but um, no I mean, not like right now but in general. In life. SHIT. Let me start over, this isn’t coming out right. Do you want to have kids? Um, you know what I mean…

<Insert long pause here>

Crush: (clearing throat) My intentions have always been to procreate, but in the last year I’ve begun to think I won’t. <Sidebar: UMm, you mean, since you’ve met me?? That’s what I was thinking, but every now and then even I know when it’s best to hold my tongue.>

Realizing this was WAY more awkward than I’d intended I went for a subject change in basically the worst possible way — 

Awkward Jean: Sooo, Friday’s Valentine’s Day. 

Crush: Assuming you are changing the subject, I’ll say this — guys are in a no-win situation with Valentine’s Day. We can squeak by, but we can’t win. I don’t do Valentine’s Day. 

Oh. Right. Guess the slippers I got him and wrapped in red heart wrapping paper is suddenly a wee bit awkward. Excellent. Right up my alley.

Which brings me to the actual day of Valentine’s Day. I had bought Crush a gift, he didn’t even wish me a Happy Valentine’s Day. My cube mate had TWO, count them TWO, bouquets of flowers delivered. I ate lunch at my desk alone and spent the evening listening to my friend’s mariachi band surrounded by other couples, flowers and heart shaped balloons. But I wasn’t alone, I had giant goblets (plural) of Dos Equis, all the chips and salsa a girl could want and a couple of my girlfriends in tow. Oh, and a small child pointed at my belly and asked if I was pregnant. I just looked at her, took a gulp of my beer and said “So you’re sayin’ there’s a chance!”

In hindsight, it wasn’t that awful of a Valentine’s Day… Well, at least it wouldn’t have been had I not established some unrealistic expectations that led me to feeling disappointed, hurt and alone (no Crush, no gift, no verbal confirmation of said holiday AND that was basically beer in my belly, not a baby). But, I kind of think that’s what Valentine’s Day does… it’s more or less a litmus test for relationships. If you get your feelings hurt — chances are your relationship needs work. If you celebrate enthusiastically and publicly — chances are your relationship needs work. If it’s basically another day and you and your partner engage in typically caring, thoughtful behavior that could otherwise take place any day — congratulations, you’re likely in a good place. 

Crush + Awkward Jean = Not a good place.

Which leads me to… 


A couple of weeks after Valentine’s Day I had an almost-perfect day with Crush. I hadn’t seen him in quite some time due to a business trip and a bout of bronchitis but finally we had a date (sorta) planned. I’d won tickets from work to a concert and invited him. He said yes! That day we went to lunch and it was nice, we had fun, it was a beautiful day, we giggled and held hands in the car… I couldn’t have written a better lunch date. Then work ended and we went to dinner at one of my favorite places and he enjoyed it and we had fun and laughed and had delicious drinks and headed to the concert and had great parking… Everything was perfect. The concert was fun, the people were great, it was an amazing night, and amazing date… And then — BAM! Awkward Jean. So close, and yet…

We’d taken my car from the office and at the end of the concert had to drive back to the parking lot for him to get his car. We sat in my car for a bit talking, listening to music, holding hands with my head on his shoulder as it got later and later… and just when he said he REALLY did need to get going this happened — 

Awkward Jean: Crush? 

Crush: Yes Jean?

Awkward Jean: Do you think you’ll ever fall in love with me?

<<Sidebar — Oh yeah. That happened. Feel free to take a moment to cringe and imbibe in a big gulp of your beverage that likely needs to be refilled at this point>>

Crush: (Patting my cheek, kissing my forehead) Do you think you’ll ever stop asking me inappropriate questions that are WAY too soon to ask?

Awkward Jean: Probably not. 

What? At least I’m honest. And, I have to give him credit, he handled it pretty well. The best part was, as he got out of the car I thanked him for coming with me to the concert, to which he replied — 

Crush: Thank you for winning tickets. (And,as he walked to his car looking back over his shoulder) I LOVE winners. 

Awkward Jean: You KNOW I’m going to over-think that! 

And I have. Well played sir, well played. 

XOXO — Awkward Jean

PS — Upcoming Posts: Why I’m a hippie on a commune, the time I bought a bed that is smarter than me and St. Patty’s Day aka The Biggest Day of the Awkward Jean Calendar Year. Until then — take care my friends. Be kind to others and be kind to yourself.