Italian food & awkward conversation

So Guy #1…”Joe” asks me to dinner.  He picks an Italian chain restaurant.  Side note: Why is Italian the go-to for guys?  Don’t get me wrong, I love me some good old-fashioned spaghetti and meatballs, but I just moved here.  Take me somewhere local and authentic.

Its technically date #2 (if you count our short “meet & greet”) and I put way too much effort into what I’m wearing.  Skinny jeans, wedges, a shirt that shows *just enough* cleavage so he’s curious but not sitting there staring with his mouth open and tongue hanging out of his mouth like a cartoon character…

What men need to understand is that women put serious thought and consideration into every accessory and article of clothing we wear on a date.  We don’t just wake up looking fabulous.  We wake up most days feeling gross and disheveled and thankful that we are the only ones who have to deal with ourselves looking like we were just run over by an 18-wheeler.  We do our hair, cake on our makeup – making sure to highlight our best features, and make sure that our shoes match our purse – which doesn’t clash with our outfit.

We cram as much as we can into a tiny little clutch bag because GOD FORBID we bring a “real purse” on a date.  Men judge a woman’s emotional baggage on the size of her purse – or so I’ve heard.  The smaller the purse, the smaller the baggage.  And let me be the first to tell you…it is DAMN NEAR IMPOSSIBLE to squeeze our “necessities” into a tiny clutch bag.  Wallet?  Forget it.  Driver’s license, credit debit card, a few bucks cash, cell phone, MAYBE a tube of lipgloss if we’re lucky.  We manage to somehow maneuver it into this tiny, toddler-sized bag and secretly hope that we NEVER have to open it that night out of fear that there is NO WAY IN HELL we are getting everything perfectly positioned in that bag again.

One final check in the mirror.  I’d do me.  Wait – WTF am I saying?  Date #2?  Down, girl.  I’m still not even sure if I like this guy yet.  Plus, in the words of Patti Stanger (aka Millionaire Matchmaker), “no sex before monogamy.”  Good rule.  I’ll abide.

I meet him outside the restaurant.  He looks nice.  Button down shirt, jeans, boat shoes/loafers.  I’m not feeling the chemistry yet, but it has been a long time since I’ve been on a date.  We’ll see.  He does not compliment what I’m wearing.  Red flag?  I’m not expecting him to fawn over my appearance but damn…I just spent more than an hour getting ready.  At least tell me I look nice.  Just a simple “Hey, you look nice” would seriously suffice.

The conversation isn’t as forced this time, but its me doing most of the talking.  He’s a good listener.  He remembers small details about our conversation the first time we met.  He’s a little stiff and nervous…and still a little awkward, but there’s an endearing quality about it.  He seems genuine and authentic.  We’re drinking water.  Part of me wished I was diving into a bottle of Pinot Noir or Chianti and that he was drinking something to loosen up a little.

Overall, I give the date a 6 out of 10.  We ended the night with a hug goodbye and he asked if he could see me again, not before telling me that my shoes made me tall.  Thanks?

I thanked him for dinner and said we could maybe work something out depending on my work schedule.

I drive home and unwind with an oversized glass of red wine.

He texts me and said he had a nice time.  I thanked him for dinner again.  We start chatting over texts a bit.  It somehow escalates to this:

“Joe” – I’m a little sensitive.  Mostly in a good way though.  But I get my feelings hurt sometimes.  Be gentle.

I now am thinking 3 things:

  1. He clearly has a vagina
  2. I would love to respond back with something witty and dirty but he may not get it
  3. I am pretty much a dude that wears a dress

WHO SAYS THAT?! Be gentle?!  I mean…women want a sensitive guy but we never want you to admit it to us after one date!  We want a manly man on the outside that actually has real feelings on the inside.  Be gentle?  Whaaaaaat?!

I’m tired so I end our text conversation but not before I click open eHarmony again and start the “guided communication” process again with a guy who would eventually become guy #2…

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