Vol Fan Puts Step-Daughter On Craigslist Seeking Date for UT-Florida Game

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This morning I tweeted out a Craig’s List ad in Gainesville which offered a free ticket to this year’s Florida-Tennessee game. 

What was the catch? Well, here was the ad:

My step-daughter’s date backed out (his loss, your gain) for the game..

1 free ticket for the Tennessee-Florida football game this Saturday (cost to me, $150) on the 40 for the right gentleman. You must be an attractive, professional, single well educated gentleman, with a good sense of humor, 25-33. You also must not be threatened by an attractive, professional, single well educated lady, (as she is). If you do not qualify, please pass this ad to a friend.

The fine print: I lied! (Sorry…not totally free). Your cost will be a modest dinner, drinks and delightful conversation with her before or after the game.

P.S. (Being a Tennessee Vols fan is not required but is highly desirable)

Only those that respond with pictures and resume will be considered! Be creative! 

Proving that every Southerner is no more than a degree removed from an Outkick the Coverage reader, this evening I was contacted by the girl in question.

Her name is Jess Flanagan, she’s a 27 year old who lives in Denver and has a bachelor’s degree in criminal justice.  

The Craig’s List ad is completely real. 

I asked her for the entire story of how it came to pass that her step-dad posted looking for a date for her and she emailed as follows:

“So my mom Brenda and step-dad Gary Yates are in the process of buying a house in Florida. My step-dad, Gary Yates is a Tennessee boy and a huge Volunteer fan with his children and grandchildren still residing in Knoxville. Gary and my mom were planning on going to the game Saturday. They had gotten two extra tickets that they had given me for the game. I had a date to go to the game with me, however the date backed out last minute due to expenses and said he could no longer make the game. Well Gary had the extra ticket and decided to post an ad on Craig’s List for it along with me being “dateless.” I said sure what do I have to lose, I am already embarrassed I don’t have a date and I doubted getting any responses. 


I didn’t actually read the post until this morning. By the time I read it, he already had 30-40 messages in his mailbox. Since then, he has had so many emails overflowing in his mail box with people giving pictures, resumes, references etc. I have narrowed it down to a few and need to make a selection possibly by tomorrow night. Gary was going to email the remaining candidates to let them know they are in the running. 


This has been an insane day that I never expected to happen in a million years. I cannot believe the emails that have come in on this. I feel truly grateful by all the wonderful guys that would like to take me out.”

I followed up by asking who the finalists were and if she was a Tennessee fan. 

“I do have the finalists in mind, however I’m still making last minute decisions on them. My step dad was going to email them letting them know they are in the running and any final words they might have. Not sure how to really sure how he is going to go about this. I have three candidates in mind. 


I am a Vol fan due to my step dad and his family. I actually have my Tennessee flag to hang outside next to my neighbor’s Georgia flag each week. I am a Bronco fan too which makes me ultimately a Peyton Manning fan. So great commonality. Obviously I will be cheering the Vols on this weekend. This is only my second SEC game to ever attend! Very excited and don’t really know what to expect. I hope whoever is chosen is ready to have a good time at the game! How do you really choose one person out of all these emails…..That is my question.”

We will update Outkick when she makes her selection. 

In the meantime, this is basically like the Bachelor meets SEC football, which, to be honest, would probably make a great SEC Network television show. 

There’s still time to get your application in, gents. 

Free tickets to a big game — okay, it used to be a big game — and a date with a cute 27 year old sports fan?

You’ve all done much worse than this. (Excluding the inevitable Internet fat guy who finds all girls on the Internet to be beneath his standards. Hello, that’s why you’re single. Loser.)

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.