Category Archives: Guy My Friend Has Dated

The “Penis Size” Guy

My friend was dating a guy and after they had been intimate a few times, he asked her if he had the biggest penis of anyone she had been with.  First of all, that is a totally weird question (guys are always obsessed with size).  Secondly, don’t ask the question unless you are prepared for the answer.  She answered honestly and said “no.”  He was a decent size, but the truth is, she had been with a guy who had a bigger penis.  He demanded to know who and she told him.  Not like it mattered, since he had never met the guy before.  After that, it was an ongoing point of tension.  He constantly mentioned this other guy’s name and was always asking about why she wasn’t with him if his penis was so big.  Penis size isn’t everything and being wildly insecure about yours, and always talking about your insecurities is a complete turn off.

The “Overpopulated” Guy

My friends boyfriend never wants to have children.  That’s a personal choice for him, but the sad thing is, my friend really wants to have children.  The weird thing is that he would completely brainwash her.  When I asked her about what it’s like with her wanting children and him not wanting children, she went off on a very seemingly-rehearsed speech about how the world is overpopulated and that people should stop having children since there’s not enough food/space whatever to maintain people continuing to have babies.

The “Control-Sleep” Guy

My friend lived with her boyfriend.  He was really weird and controlling, insisting they go to bed at the same time each night and wake up at the same time every morning.  So he would never let her sleep in, or if he wanted to sleep in, he would get mad that she would dare get out of bed before he woke up.  This meant if there is a game on he wanted to watched, she couldn’t go to bed while he stays up to watch it–she had to stay up until he was ready for bed. This was definitely a red flag–never be with someone who controls your sleep schedule.


The “Free Trip” Guy

My friend was going on a trip to Chicago for work.  Her boyfriend was originally from Chicago and his dad wasn’t doing so well.  She thought it would be nice to pay for his plane ticket; he could stay in the company paid hotel with her and he could see his sick father.  I don’t know how the conversation came about, but in her mind that’s what she was doing.  I thought that was extremely generous and he would not have been able to afford a ticket and a stay to see his dad otherwise.

They landed at the airport and were getting their luggage.  She said she asked him how they would get to the hotel–maybe he could go to information and ask?  He replied in a snarky tone“this isn’t my trip.”

So…he thought he was doing her a favor by coming along?  I would have been so offended and sent him right back on a plane.  My friend didn’t do that, but she was pretty pissed.


The “Horrible Texter” Guy

My friend had a thing with this guy, and it wasn’t totally working out so they ended it.  He sent her this long sob story about how he misses her and thinks about her etc.  She assured me that he was not drunk.  In the text messages she showed me, there were a ton of grammatical errors and spelling mistakes. No one is perfect, especially when they are emotional, but if you are trying to win back a girl, you should make sure you seem pretty intelligent and educated.

The “Early-Riser” Guy

I have a friend who has an insanely busy job.  On the days that she has off, she would like to sleep in. She tells her boyfriend to please let her rest, she really needs it.  He is an early riser.  Every time, without fail, he wakes her up super early and wants to cuddle or more.  She is grumpy, gets mad at him, just wants to sleep in and they end up getting into fights.  He says he wants to spend time with her on her days off, so he wakes her up early.  He is specifically asked to NOT wake her up early, and fails to do it.  It’s not that hard to just let someone sleep in.

The “Gold-Digger” Guy

I would often double date with my friend and her boyfriend.  It started to be a trend–my boyfriend and I noticed that she ALWAYS paid when it came time to split the check.  I’m all for strong, independent women, but he would never even offer or pretend to take out his wallet.  Every time the check came, he would sit there and she would pay for it.  I guess she made more money than him, and he was perfectly comfortable letting her take the reigns with the money?  One time the check came while she had left the table to go to the bathroom. Instead of waiting for her to return, or taking out his own wallet, he literally reached over, grabbed her purse, took her wallet out, slid out her credit card and put it down on the bill. What?! I understand that she was probably the breadwinner and probably paid for most things, but at least wait two minutes for her to do that herself, don’t reach into your girlfriend’s’ belongings for money to pay for your meal.

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 “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.

The “Never Living Together” Guy

My friend had been with her boyfriend for two years.  They did not live together and never talked about the future.  I thought it was a little unusual but to each his own.  She told me that they have a friend who met a guy four months prior and moved in together.  My friend and her boyfriend when to visit their new place and she thought it was so cute and nice that they moved in together that she decided to bring it up to her boyfriend.  When they got home, she mentioned how nice their place was and did he think they would ever move in together.  He said “maybe we can talk about it in two years.”  That was literally what he said! That maybe in two years, (after being together for two years already) they can discuss the possibility of moving in together.