Today's Most Undateable Man in Chicago is:

About The Invisible Man:

...in ALL the wrong places, obviously

Why I Feel Undateable:

I got married over a decade ago for what seems now like a quick minute, and ever since then this special lady has taken it upon herself to wage a continual legal battle over nothing of merit, causing constant disruption and hassle in my life. As a result I have to work about 12+ hours per day to keep my lawyers dining at fancy restaurants which makes my schedule pretty challenging.

I haven't had a "romantic relationship" in over six years. I'm awkward when it comes to pretty women in my vicinity, I turn into jelly and it's almost impossible to break the ice or for me to be myself at these moments so I usually just end up saying embarrassing things and running away.

I pay for dating apps and I've "swiped right" on thousands of women but I never get matched. Hundreds of my genuine, thoughtful messages have gotten me almost zero responses. I feel like I'm invisible.

I am swamped with lingering real estate issues I can't seem to get out of, which has me doing things like rehab, showing apartments or going to court all the time to keep everyone happy amd the city off my back.

I am a single dad and I love time with my young son more than trying to get back into the dating thing, so it makes it too easy to just give up on the idea of meeting someone. I also have shared parenting days throughout the week so it's hard to get blocks of time or to be flexible to do things on a given schedule.

At this point I'm starting to wonder what the benefit of a relationship even is, and whether it can still be something magical or if all relationships settle into a "comfort zone" where basically it just means you end up sleeping in proximity to each other every night. There's got to be more to it if I'm going to go there again. Also, the thought of having to give up half my stuff or go through court again if it doesn't work out is enough to make me sick.

I don't know what to do with myself as a 50-something single dad, I feel like a dork going out alone and women look at you like you're a predator. The look in their eyes makes you feel like a stalker, and once that's in your head you try to actively not look that way and it only makes it worse. I feel like I'm never going to meet a quality woman worth my time unless she somehow drops right out of the sky.