When I arrived in Chicago, I decided to get my feet wet in the dating pool. If it taught me anything, it’s that there’s a different type of breed when it comes to men in the 21st century. I got some of the strangest messages and went on some interesting dates. Seriously, what is wrong with men today? Anyway, let’s sit back and enjoy all the crazy messages men sent me in the last five months.

Picture this! Myself and a guy are having brunch at a chic restaurant in Wicker Park with a family of 5 sitting next to us.

Him: Last night I went to a party.

Me: Oh cool! What was it for?

Him: It was a BDSM party so I just walked around and watched people having sex.

Me, trying to enjoy my orange juice and pancakes while the grandpa from the family next to us is staring me down.

Him: So do you want me to go down on you after this?

Me:

That was the most memorable brunch ever!

“I had a nervous breakdown so I don’t know if I can do this anymore.”

“My grandma died so I’m going to focus on myself for now.”

“I don’t want to end up as a subject on your podcast or blog.” (mind you, we just started talking)

I hope I’m alive to make this happen.

Guys who have expectations but don’t put any effort to make it happen.

Nothing like pure excitement!

Let’s just get straight to the point.

The message that got me thinking about casseroles and why people are obsessed with them.

That time I learned what OM ing was.

Sometimes it’s hard to take a hint.

This was a killer conversation.

Once in a while you get a really nice message.

They say you must kiss a lot of frogs before you meet your Prince Charming but what do they consider this? I think this is below frogs.

It’s sad times when you and your friends just want a decent human being and men continue to miss the mark. The bar is so low and yet, they can’t seem to attempt to touch the pole.

Have any funny dating stories from this year? Share in the comments!