What are you doing for Valentine’s Day?

How many times have you heard that recently?

Are you tired of saying “I haven’t made plans yet?

Well have I got a deal for you!

Do you ever dream of the day when your knight in shining armor comes riding up to you on his battle steed? Do you long to sit in your very own castle and dine with other royalty? Do you secretly hope Westley from The Princess Bride will come rescue you? Well all of that can be yours on this Valentine’s Day because I am now accepting applications for my latest contest.


This contest will be a series of dates that will be happening occasionally in upcoming months. I can promise that all dates will be interesting and pretty different from most normal dates. I promise that some will be cheesy and some will actually be pretty amazing. I will have no control in who my dates are, so all inquiries must be emailed to my Selection Committee at  I have been held down and tortured until I gave up my deepest and most sincere desires and an application has been created to indicate what I think is the perfect woman. So I encourage you to please email and someone from The Win A Date With Jerry Selection Committee will get an application right to you.

Act now! Supplies are limited!

“But Jerry! What am I applying for?”

To celebrate our first Win A Date With Jerry Contest, we’re going to be going old school. Medieval in fact!

Are you ready watch knights battle to the death for the hand of a fair maiden. OF COURSE YOU ARE!

Are you ready to see the forces of good and evil try to conquer each other? OF COURSE YOU ARE!

Are you ready to have a bar maid ask you if “Ma’Lord and Lady would like another Pepsi”? I’M BETTING SO!

If all of these things are appealing to you, then you’ll be excited to know that our inaugural event is going to be held at:

By The Way: All dates will be double dates with two of the most amazing people I know. Jared and Meredith Roman! So I would recommend applying just to hang out with them…


~ by jtcrespo on February 3, 2009.


  1. It’s like your own personal version of Win a Date With Tad Hamilton! If you haven’t seen that movie, maybe you should set up watching it as one of your dates…. 🙂

  2. Jerry – this is awesome. Want me to pass it along to my friends? They are all pretty amazing!

  3. I’m in. How much?

  4. Jamie – There will be no watching movies on my dates. They are all interactive!

    Jessica – Tell it far and wide. I’ll honestly be surprised if a single application is turned in.

    Chris – It’s free, but if you get scared I won’t hold your hand…

  5. Is there an age requirement? If not, Audrey would like to enter.

  6. LOL – Have her fill out the application. As far as I know, all entries will be considered.

  7. Jerry, you rock! I so want an application. For sure, I will win cause that’s how I roll ;)~

  8. HAHA! this is awesome! you’re gonna have a blast! any gal would be lucky to win a date with ya!

  9. I am so excited! Medieval Times is going to be some great people watching that night! Also, if you think Jared and I are some of the most amazing people you know, we need to get you out more 😉

  10. OK, Jerry . . . . time’s up . . . . .who is the lucky winner?????

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