Cupid’s Undie Run + Week 6 Boston Training

Cupid’s Undie Run “Race” Recap


The tribe is fast.  The tribe is strong….



The tribe is also insane.  What else do you call willingness to run outside in your underwear on a day with a windchill advisory?  You call that insane.  And I love it.


The Cupid’s Undie Run is a fundraiser for the Children’s Tumor Foundation.  The founder, Bobby Gill, was featured on the cover of Runner’s World a few months ago, and the organization has grown considerably since the first run in 2010.  In addition to being a fundraiser, The Cupid’s Undie Run is part party, part run, part party some more.


The event took place at John Barleycorn up in Wrigleyville.  Upon arrival, participants checked in to get an official participant’s wristband and any other prizes they earned through fundraising.  I want to send out a huge THANK YOU to all who donated to my page!  Because of your generosity, I raised $481 dollars and earned some pretty sweet swag: “I’m With Cupid” socks, underwear, sunglasses and most importantly, an open bar.  However, immediately when I got to the bar I asked them to change the TV to the Olympic Marathon Trials and then ordered a drink.  Priorities. 

Not pictured (the most important part): the open bar

After about 2 hours of pre-partying, there was a costume contest and prizes awarded for the individuals and teams that had raised the most money.  November Project was asked to lead a bounce before the run to pump everyone up, but it was too much of a cluster-cuss to coordinate.  Initially they told us to get on the stage, but then they yelled for us to go outside to the front.  Suddenly everyone was rushing towards the door in excitement and as soon as they got outside started sprinting along the course.  So the bounce went out the window as we sprinted to get to the front.


We exited John Barleycorn, headed north to Addison, then took a right to go to Sheffield. They didn’t block off the streets for us, nor did they clear the sidewalks of pedestrians but we definitely stopped traffic!  Imagine you’re driving next to Wrigley Field and suddenly there are around 200 people in their underwear sprinting by.  I bet you’d hit the brakes too.

When we got to Sheffield we turned right again and headed down to School St. before making a u-turn and heading back north to Clark St. and then back to the bar.  I remembered to start my watch halfway through the run, so it didn’t record the whole thing, but the whole course ended up being only .9 miles.  Within 6 minutes we were back at the bar.


I wore a sports bra and bikini bottoms, with high socks, the new yellow November Project buff, and thin pink gloves.  Initially I had been so worried about being cold, but I hardly noticed the cold once I got out there and started running.

Photo Credit: Tiffany P.


After the run, we all reconvened in the bar and spent the rest of the afternoon laughing, drinking, and taking pictures.  We were among the last of the participants to leave.

IMG_6303 IMG_6309
usain bolt
Photo Credit: Chris C.


The Cupid’s Undie Run was definitely one of the craziest things I have done, but also one of my favorites.  I absolutely loved the experience of fundraising and it pumped me up to get involved with it more.  I also absolutely love the positive goof-ball energy of November Project.

Photo credit: Kevin W.


I would highly recommend participating in the Cupid’s Undie Run next year!  I know I will be! 🙂  And if you’d like to check out November Project come to the Totem Pole at 6:28 on Wednesday mornings or the Bean at 6am on Friday’s.  I promise you’ll love it just as much as I do!

Happy running,


Week 6 Boston Training Log

(Catch up on previous weeks here)


Monday:  9 w/ 5@Tempo. Day’s total: 9.05mi, 7:24 pace.

  • AM: Supposed to be at half marathon pace (6:50 for me) but I found it a struggle.  Splits were 6:58, 6:50, 7:02, 6:57, 7:02


Tuesday: EZ 7. Day’s total: 7.27mi, 8:33 pace

  • AM: Met with Clocktower for a few super slow miles.  It had snowed the night before so there was a good dusting on the ground, and it felt like running in sand for some portions of the route.



  • PM: Hot Power Fusion at CorePower.  An ok class, basically yoga but heated.  It wasn’t flow-y enough for me.


Wednesday: Tabata class + Speed (4×1 mi). Day’s total: 8.17 mi

  • AM:  Wasn’t weatherproof enough to make November Project this morning (embarrassed), so I went to a tabata class at I.D. Gym instead.  All strength based and very little cardio, but I learned some new exercise ideas that I really liked.
  • PM:  I waffled all day about going to speed or doing it during the day when it was going to be warmer.  Convinced myself I would feel much better seeing my friends and running with the group so I waited it out.  These intervals were supposed to be faster than 5k pace (still have no clue what that would be but I guess 6:25 based on my 10k pace).  Again I struggled to get my pace fast like that; splits were: 6:43, 6:41, 6:41, 6:35.  Each time I got faster, I just wish it had been closer to my goal pace.


Thursday: XT/Rest. Day’s total: 0

  • AM: Hot Buddah Burn. Later in the day I was huffing and puffing trying to get up the stairs because my quads were so tired.  Thanks for the great workout, Cheyne.


Friday: EZ 9. Day’s total: 9.26mi, 7:58 pace

  • Did ~2.1 miles at NP and 7.16 miles home.  NP was very ab heavy- I guess they were trying to prep us for the Cupid’s Undie Run!


Who says winter means running on the treadmill and giving up this beautiful city?


Saturday: 18 miles. Day’s total: 17.4mi, 7:42 pace

  • AM: Fleet Feet cancelled the run out in Barrington because the temperature was in the negatives with the windchill.  So what did I do?  Called up my parents in Highland Park and asked if they’d be willing to bring me water if I drove out there to run on some of the hills along Sheridan Rd.  I ended up parking at the train station and doing 3 loops of 6 miles so I could stop at the train station and get water.  I told my mom that I’d check in with her around 9am, and when I didn’t do that (I couldn’t get my phone out easily from underneath all my layers), she went out and started driving around looking for me haha. I got pretty cold towards the end, so I cut the last loop short.
  • PM: Cupid’s Undie Run


Sunday: EZ 8 Day’s total: 8.17mi, 8:10 pace

  • AM:  I could have done either 5 or 8 easy miles based on the plans, but opted for 8 since I missed a few miles yesterday.  HOLY WIND!
  • PM: Bikram Yoga.  Always feel so refreshed ending my week with this.


Week 6’s total:  Planned mileage: 58.0 Actual mileage: 59.32mi

  • Did a much better job sticking to the mileage and taking slower recovery runs too.

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Pete B

The Cupid’s Run looks like it was a blast. I’m with you – why run on a treadmill when it is so beautiful outside?!