What Not To Say To Women

A smart, funny, attractive guy who not only admits to being clueless about women but is willing to share his dating diary? Tap your inner Bridget Jones by offering him your advice.

I'm a victim of the language gap between women and men. I've been known to put my foot in my mouth by blurting things out that seemed so right at the time.

My friend Justin's girlfriend Blair came over before a Christmas party we were having. She spent a lot of time in his room getting all made up for the occasion. My first mistake was ignoring the fact that an apartment Christmas party is the kind of event where girls like to look good — or be told they look good at least. Blair emerged from Justin's room in a floppy looking tank top. Upon her entry into the room, I looked her up and down and stated flatly: "hmm, you're looking frumpy tonight". I truly believed that the word "frumpy" did not have a negative connotation. I thought it meant having a baggy appearance. OK, maybe that doesn't sound that great, but I certainly didn't know it meant this:

frump, noun, A girl or woman regarded as dull, plain, or unfashionable.

frumpy, adj, primly out of date

Ever since that night Blair sarcastically asks if what she is wearing looks "frumpy". Maybe I should stick to using words that I am 110% sure of their meaning — especially when it comes to critiquing a girl's outfit. Sorry, Blair.

An even more disastrous event occurred when I was trying extra hard to be nice to a girl about her outfit. A really cute co-worker of a friend of mine named Courtney was out with us one night. I decided to try one of my favorite lines: "I like your outfit". But this was Courtney, so she deserved a tailored (no pun intended) custom "I like your outfit". I walked up to her and said:

"Wow, you look great tonight. I like your outfit a lot. AND, it looks like you didn't spend much on it either."

I then stepped back to admire my work. Something didn't seem to jive. Later on, I found out that Courtney was crying in the bathroom over something I had said. Her friend explained to me that I had called her outfit cheap. I was at a loss on this one. I thought of all the times I had heard the following conversation:

Girl 1: "Oh wow, girl, you look great. Love that dress."

Girl 2: "I know, right? Shoes? Target. Dress? Target. Bag? Target. $34 for the whole outfit."

This was what I was going for. Why are girls allowed to brag to one another how little money they spend on an outfit, but guys are not allowed to say: "hey great job looking that good and not spending much money to do it." I'm usually willing to admit I'm wrong, but not this time. If anyone can shed some light on that one, I'd appreciate it.

The Morning After

Girls are so sharp, and I keep forgetting it. I keep thinking they are like me: only half listening…if that. Instead, they are extremely attentive, detail oriented and organized.

One girl that I went home with one night (against my will) really called me out. As the sun was coming up, I desperately wanted to be anywhere else on the planet besides her bed. I got up and started getting dressed. Apparently, I hadn't stayed as long as she'd like. She sat up and exclaimed: "oh, what? You're just going to take off now?"

I was startled. I figured, I'll say what we are both thinking instead of giving her bullshit. She'll think it's so cool that I was so honest and that I said what we are both thinking. So it was:

"Course I'm leaving. I know you don't want to see my stupid face first thing in the morning."

Silence. Then she said: "get out. Just get out."

OK, so I misread what she was thinking.

Another girl that I pleaded and pleaded with to come back to my place one night so that I could kiss her ended up spending the night. The next morning, I had no intentions or really pursuing anything. In fact, I was wondering why I had done all that pleading. I did plan to call her though, because perhaps with some time together it would become apparent why I did all that. As I said goodbye to her I mentioned:

"So, I'll call you mid-week".

That seemed to be a harmless enough statement until our mutual friend Lauren called.

Me: "Hello?"

Lauren: "I'll call you mid-week?!!!"

What I meant by mid-week was Wednesday. I wanted to call her on Wednesday because, on Sunday morning, Wednesday seemed like the right time to call her. I don't know why I shrouded Wednesday in the mysterious cloak of "Mid-week". I guess I wasn't paying attention. Unfortunately, other people were. That's another one where I don't quite get what I said wrong.

When I was in Rome I took advantage of the old "what happens overseas stays overseas" mentality. I walked out of a bar up to a cab by myself, met a girl who spoke English (I guess this is all it took for both of us at that moment), and jumped into a cab with her. Before I knew it, we were at her hotel room having sex.

The next day I woke up and actually took some time to get to know this girl I had mistakenly been intimate with. Among the things I learned about her was that she attended Xavier University. It came time for me to leave. Suddenly, an unsettling idea entered my mind: two people who were so close just hours before were about to part ways forever. This called for one of my brilliant exit lines (similar to the ones you've read above) because the awkwardness had to be fixed by my mouth.

As I slipped out of the hotel room door, my mind jumbled and turned…"Xavier…it's April…March Madness…Xavier's in the tournament…"and, as the door closed I poked my head in:

"Well it was great meeting you. I hope Xavier does well in the NCAA tournament."

And the door was shut.

With the mixture of stupid things I've said: trying to fix the moment, letting my opinion fly, trying to be honest…I wish there was some way I had of mentally editing. I know better than to try to pull a fast one on a girl, but it's really a helpless feeling when I realize that they are indeed listening to just about everything I say.

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