Preface: As with any easily accessible route, especially on a face that has existing lines, it's certainly possible we weren't the first ascentionists, but from what I could gather, I believe at least the first pitch is new. Please update the page or message me if you know of prior ascents! Also, I'm writing this over 3 years after our ascent, so hopefully my memory isn't too bad. I'm mostly adding this as a way to let future curious parties know how serious the climbing is - or you could stop reading now and experience a similar onsight adventure.

Background: In an attempt to rack up additional "birthday pitches," after having onsighted the other routes at the wall, I saw the thin hands crack splitting the small roof and asked Eric if he knew what route that was. He thought it might be the original Yoder route up the wall, but I later learnt that route, "Heads," starts further left and doesn't appear to tackle this roof. Due to this not being "Heads," and the terrible rock quality we found, I thought the name "Tails, You Lose!" was quite fitting for this route.

P1: Head up the slab towards the hand crack splitting the small roof (arm's length long), either boldly heading directly or finding gear out right (be sure to extend!) before working your way back left to the crack. Pull the small roof and continue on easier terrain until you can build a solid enough belay. (5.9+ R)

P2: Head up and towards the orange rock with an undercling flake bordered to its left by a short, shallow corner. Eric built a belay at the base of the corner. (total guess but maybe 5.6/7 PG-13?)

P3: Climb up to the undercling flake and use it to traverse right. Rad undercling hand jams with friction feet! Continue traversing until roofs no longer block the way up and then head up until rope drag becomes too bad and build a belay. (There were jugs beneath the flake but I ripped one, maybe two, off on my first go at leading this pitch. Fortunately, I was already very suspicious of the rock and placed a cam before traversing which prevented a factor-2 fall onto the anchor. I then sent the pitch starting again from the belay - I can't remember if that first piece was easily cleanable from the anchor, so not sure if I pinkpointed or redpointed the pitch...) There's an obvious weakness through the roofs instead of traversing all the way right which was very attractive, but likely unprotectable - perhaps someday this vision will be climbed - maybe by you?? (total guess but maybe 5.8+ PG-13/R?) I'd need to check the guidebook again (which I don't have), but maybe this is the crux pitch of Heads?

P4: Follow the path of least resistance up and left, eventually running into some newly bolted line to the left (from what I remember, the bottom pitches hadn't yet been bolted back in 2019). You could maybe continue between this bolted line and Condorphamine Addiction on traditional protection, but Eric clipped some bolts and I believe used the anchor on top to belay me up. (total guess but maybe 5.6/7 PG-13?)

Closing thoughts:

• I remember immediately after the climb thinking this was 5.10, but I think fear likely inflated those original impressions. Nostalgic memories of the Gunks, makes me think this could get 5.7 there. Go into this with an open mind, expecting engaging, moderate climbing.
• I have never yelled out "Rock!" so many times on a climb. Perhaps best to save for a day when there aren't a bunch of folks waiting in line at the base to climb Condorphamine Addiction. If the rock quality wasn't so bad, I'd give this 2 stars. Probably really good practice if you're training for alpine routes ha
• I led first and swung leads with Eric. Everything was ground-up, onsight. Eric never weighted the rope. I weighted the rope in the fall described in P3, but then successfully sent the pitch.

Small roof split by a crack to the left of Condorphamine Addiction