Monthly Archives: September 2016

The “Casual Friday” Guy

I hadn’t been dating this guy for that long, but the first time he slept over on a weeknight it was a Thursday.  We are both in the corporate world, but I happen to have casual Fridays in my office.  I put on some jeans, flats and a nice blouse.  I came out of my room, he literally looked me up and down and really judgmentally said “…jeans to work?” Yeah, you’re not my boss and I have casual Friday at my office.

The “Crier” Guy

I was having some major issues with my boyfriend and we both knew it.  One day when we were out at dinner, he brought it up and asked me why I am unhappy.  I was open and honest and listed all the things going wrong in our relationship.  I was stunned when he looked at me and burst into tears in the restaurant.  I didn’t know what to say so I just stared at him and kind of ate.  It was SO awkward.  (This was years ago when I was much younger and much more awkward).   He went to the bathroom and when he came back, I asked him if he was ok, and he said he just felt like he was being totally attacked.  He brought it up, and he asked me what was wrong! I was just being honest, which I thought was the right thing to do.  I don’t know why he asked if he didn’t want to hear the answer.

The “Adventurous” Date

My friend met up with this guy from an online dating site.  The first dates are generally short and sweet, just to make sure they are who they say they are and that maybe a second date will happen.  After the first decent date, they spent a few days with nice and flirtatious text messages.  He texted “would you like to go out again? We can have an adventure.”  She told me about it and was happy that he asked her out again, and we mused about what kind of “adventure” he could possibly be planning. A nice hike or a cool new restaurant?  Who knows.  She responded that she would love to and they decided on a day about a week out.  Two days before this “adventurous” date, he texted her and said “so what did you have in mind? I can meet you where ever”  Wait…he asked her out, he specifically said they would have an adventure and now he wants her to plan it? First of all, if you are asking someone out, take some initiative and plan it.  Secondly, if you specify that it will be something awesome, you should probably already have something planned.

The “Star Wars” Guy

My friend went on a date with this guy right around the time the new Star Wars movie came out.  The topic came up and he said he HATED all the Star Wars movies, with a passion.  She was surprised and said she really enjoyed it and most people she know like it or at least think it’s decent.  She expressed that he is the only person she knows who absolutely hates the Star Wars movies and his exact response was “Well, I guess that shows how much more awesome I am than everyone else.” I asked her if he was kidding or being sarcastic, but she was sure he was just a cocky asshole.

The “Car Light” Guy

The guy I was dating and I got invited to a house party.  Due to our work schedules, we decided to drive separately.  I got there first, went inside and mingled. Then he came in, and we all hung out.  One of our friends came much later.  He walked in, and came right up to me and said “hey, I saw your car outside, your interior light is on.”  I was surprised, and thankful that he told me! The guy I was dating immediately said “oh, yeah I noticed that on my way in too.”  I was kind of weirded out.  I said “You knew the light in my car was on, but you didn’t say anything?”  He just shrugged and walked away.  It is absolutely common courtesy to tell someone you know–especially a friend or someone you’re dating that their car light is on! My battery could have died.  I was so offended that he did not immediately think to tell me and then just shrugged it off.


The “Playboy Model” Guy

I was dating this guy for a while and things were up and down but going decently.  I can’t remember why, but one night we were both busy.  I was spending time with family and he had some event he needed to go to.  We did text a bit throughout the night, but the text that made it a major “red flag” was that he said “I’m here hanging out with my playboy model friend and all I can think about is you.” That is a really weird way to pay me a compliment.  So glad you could tell me about this sexy woman that you are spending the evening with.

The “Drinks on Tab” Guy

My friend went out with this guy who bought her dinner.  She said she thought he was nice.  They decided to go to a bar after, and since he bought dinner, she said she would get his drink..  They ended up hanging out, playing pool, talking and having a great time.  He kept going back to the bar to get drinks and kept bringing her one.  She thought they were really hitting it off and the night was going well.  Until she closed out her tab at the end of the night and realized that he had put every drink on her card.  Without asking.  He literally just kept walking up to the bar to order drinks for himself and her and just kept putting it on her tab.  Her bill ended up being huge.  He didn’t say anything or offer to pay her back.  She told me she thought she made it clear that she offered to buy a drink not drinks for the entire night.