PeeWee Herman Helps Ben (Founder of The Flippist) Propose

PeeWee Herman Helps Couple Propose (6)

How We Met

Couples tend to remember and celebrate their first kiss, their first date, or the day they got married…sure we mark those occasions, but one of our more special dates is our Pee-wee-versary on January 28th 2010.  That’s the day Pee-wee Herman helped us propose.

Back in ‘ye olden days’ of AOL profile pages, I was just searching their directory for interesting people with similar interests to talk to, so I search these three keywords: Pee-wee Herman, Prince, and Radiohead.  Other than my own name, Summer was the only one to pop up with that combination. We started emailing, which led to becoming snail-mail pen pals, eventually we met up and hung out in person (she was in St. Louis, I was in Detroit). After dragging all that out for over a year, finally we started dating.

So among other factors, Pee-wee Herman was the main thing to bring us together.  We are both crazy super fans, and both grew up watching his movie “Pee-wee’s Big Adventure” and his Saturday morning kids show “Pee-wee’s Playhouse”.  I hoped that searching using the words Pee-Wee Herman would help me find someone that (like Pee-wee) would be artistic, creative, funny, weird, corny, sincere, sweet, and totally 100% unique.  That’s about exactly what I got when I found Summer.

PeeWee Herman Helps Couple Propose (7)

How He Asked

After dating for around 5 years, the perfect opportunity came up for me to possibly incorporate the REAL LIVE Pee-wee into the proposal.  It had just been announced that Paul Reubens would be bringing back his Pee-wee character for a 4 week stage version of Pee-Wee’s playhouse live in L.A.  We lived in Chicago, and were both broke students without jobs, but knew no matter what…we had to get there to see him somehow. I knew it was a long shot but I googled any name I could find that was associated with the show; writers, producers, actors etc. and made my case to let me propose to Summer with the help of Pee-wee somehow.  Summer and I are both artists and have made an obsessive amount of Pee-wee related art in our days…so I made sure to include all that as well along with the written groveling.

After I don’t recall how long, it’s kind of a blur…weeks maybe, eventually…PAUL FREAKING REUBENS called me up and agreed to help out.  I couldn’t believe it.  I had a voice mail from my hero.  So from there we worked out a whole plan involving a fake raffle to get us pulled up on stage where Paul would then turn it over to me an I would pop the question.  So eventually the day came, and it was the weirdest most magical day of my life, seeing the Playhouse in front of my own eyes, knowing that at the end of the performance I was going to be up there on the stage.

PeeWee Herman Helps Couple Propose (8)

PeeWee Herman Helps Couple Propose (9)

It all went by so fast but thankfully Paul Reubens arranged to have it filmed so we now have that memory to review forever.   Paul couldn’t have been any sweeter, any more generous and accommodating.   He later said that he had always wanted to be part of a proposal (and I’m sure he’s had many requests ) I’m just glad he let us be the couple.

PeeWee Herman Helps Couple Propose (5)

Like I said, we didn’t know how we were going to afford being able to get to LA and get tickets…but I made it work somehow.  I sold paper mache Clockys on ebay to pay for the trip out there.  As you can hear in the video, Paul (jokingly) threatened to sue me for making them, but then eventually requested some to give as gifts.  Just an awesome awesome dude. PLEASE watch his upcoming new movie, “Pee-wee’s Big Holiday,” produced by Judd Apatow coming to Netflix on March 18th.

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