The Rejection Therapy Challenge – Week 2

The Rejection Therapy Challenge – Week 2

The plot thickens as I continue into the 2nd week of the Rejection Therapy Challenge. (I posted previously about week 1 rejections.)

A recap for new readers: I’ve taken on a 30 day challenge where I need to get personally rejected by someone every single day. I was inspired by to try it and thought it might be fun and help me get out of my comfort zone. I’ve been documenting this stuff on my blog.

INSIGHTS: I think the rejections this week are more interesting and more “real” than last week which I think is great (of course you can be the judge). I’ve also noticed that the challenge is making me more open to talking with strangers – because they might hold a rejection opportunity. It makes me more aware of my surroundings in general. I see that I’m exposing myself to serendipity, as Paul Buchheit recommends. It’s fun, a little stressful at times and as a fringe benefit, it’s makes for a great introductory story when meeting new people.


We were out for isocket team lunch and noticed a really nice, brand new Jaguar parked out in front of the restaurant. Later when we’re finishing up lunch we see the owner talking to someone and getting ready to drive off. I run outside and tell him I think he has a really nice car and ask if I could sit in it. He agrees. We talk briefly about why he got the car and how long he’s had it. As he push button starts the car, I ask if I could take it for a spin – he laughs and says no. REJECTION!


Today I got a free V8 with tea infusion from some promoter on the street. Later I run into a homeless guy who  asks for change. I offer the V8 bottle and he refuses! I even ask again “are you sure?” in my most persuasive voice – still no. REJECTION!

Later I was working at Starbucks before a Doctor’s appointment and ended up taking a 25 min phone call with a potential customer. When I ended the call, the old lady sitting across the table from me leaned over and said “I don’t mean to be rude, but I don’t think that phone call was appropriate.”

She then proceeded to lay into me about how Starbucks isn’t my home office and how phone calls ruin the coffee shop atmosphere. I took it all in good stride and she ended up shaking my hand as she left – I tried hard not to be say anything to provoke her. More amused than anything else at the UNPROMPTED REJECTION!


I was eating lunch at a small Vietnamese place in Burlingame and started joking with the owner about how maybe I could do the dishes instead of paying. She kind of went along with it at first, saying I’d need to wash 8 buckets in 2 hrs and dry them etc. Since that was not really a rejection, I decided to push it by actually pretending like I was going to do it.

At the end of the meal I said “OK, let’s do this!” I took off my jacket, put dishes into the tray and started busing the table. She’s lets me do all this and I start getting nervous. I walk into the back room to start washing the dishes and finally she’s says “Alright, you can stop! I was just joking!” I smile, and silently whisper thanks. REJECTED!

Later that night I was at dinner with friends in Palo Alto when I saw a girl who kind of looked someone I had met a while back. I tried saying her name and seeing if she responded. She didn’t. But she was so *almost* like the person I knew that I just went up to her group and asked if her name was Rui. “Nope it’s not.” she says.

I ask her name. She says she won’t tell me but shell let me guess. The guy next to her says it starts with a “J”. I guess Jessica. Wrong. Jennifer. Wrong. Then she tells me in a condescending tone that her name doesn’t even start with a “J”. EPIC GROUP REJECTION!


This day wasn’t great in terms of rejections.

I visited the Stanford gym to see old teammates and chatted with our new athletic trainer. I asked the Stanford trainer if she could stretch out my rotator cuff. She’s not really supposed to work with non athletes but she did help me out. Then I asked for a neck massage – her answer? “No.” REJECTION!

On Thursday, I had texted the girl I had met on the train on about getting drinks and she never responded. I then called her on Saturday to confirm that this was indeed a rejection. I got her voicemail and no callback. BLOWN OFF REJECTION!


I buy tea at a cafe and the barista mentions she really wanted to try the flavor I had gotten (white/green tea blend). I suggest letting her try. She demurs then goes to serve other people. I wait till the tea has steeped and she’s free – then walk back over and say “No serious, have a sip. I haven’t touched it!” Still no. DRINK REJECTION!


I was frustrated today because I made a couple of asks during the day (both at work and at the gym) and got approved. I then went home and had a long phone call with Jason Comley, (the guy behind which was great, but then I was running out of opportunities to get rejected.

Desperate, I started calling random (415) numbers seeing if I could get a stranger to help me with something (ask about Halloween activities, or recommend good movies to see). Ended up actually talked to 3 people – had a conversation in Mandarin with one guy, baffled a now-living-outside-SF guy and was told to see “Inception” by a third guy. Felt kind of bad about this one for annoying people and still getting NO REJECTION!

I then called a bunch of friends asking to borrow their car to drive to LA (which I actually needed!) but people weren’t there or had legitimate excuses for why I couldn’t use it (too old, needed repairs).

Finally, I went on chatroulette and after getting skipped a ton, talked to some dudes for a while and asked them to do a dance for me. They said no. REJECTION!

I was doing a lot of the car phone calls and chatroulette stuff in my roommates room and when I finished, he said “ok great, now get the fuck out”. Probably the day’s most solid REJECTION!


I was a little annoyed with what I had to go through to get rejected on Monday so I deliberately stayed low key and only asked for things I actually wanted. For example, I asked a friend if I could join his dinner plans with another mutual friend and he actually refused me. It was a polite but definite REJECTION!

Thanks for reading this far! What do you think about this week’s rejections?

>>EDIT – I almost forgot – probably the most important thing that’s come out of this so far is that I told a girl that I actually have a huge crush on (someone I know, not a random stranger) that I like her. Her response was “Oh great.” =) Not quite a full on rejection and obviously I could have forced a stronger response, but I think it was something where I genuinely was afraid of getting rejected. And I went for it.