The Rejection Therapy Challenge: Week 1

The Rejection Therapy Challenge: Week 1

My first week trying out the Rejection Therapy Challenge

I’ve been turned down, rejected and blown off for seven days straight. I’m thrilled.

In my last post on the Fear Scorecard, I discuss something I discovered via Hacker The site offers up a challenge with one rule: Get personally rejected by someone everyday for 30 days. The goal, according to its Creator Jason Cowlely is to reduce the fear and pain felt around rejection, encourage more open and “risky” social interactions and reap the many rewards that this comes with. (See the about page)

After reading it, I got really interested in doing it. I thought about how I even though I can tolerate a lot of physical pain and academic and career failure, I really don’t like being rejected. This is an area I’d like to tackle and conquer.

So I went for it. The results of just one week have been very interesting and I’ve decided to share them on my blog and see what happens. I dashed off emails of my rejection attempts each day to a couple friends to keep me on track. They’ve been tweaked for readability. Hope you find them interesting and they inspire you to give this a shot.


Warmup: asked a lady in airport store if she could “Get me one of these headphones in a different color.” She said no – that’s all they had. SOFTBALL REJECTION!

Main ask: on my Virgin America, I asked the flight attendants if I could fly first class. At first they said “You sure can!” and I followed with “For free” which they rejected. But they were nice about it: “It’s a short flight and even we don’t get free upgrades!”. REJECTION!


Asked a total stranger for their conference schedule guidebook because I didn’t get one. After a big “Pleeease?”, she gave it to me. Damn! But it started a nice conversation. REJECTION FAIL!

Then asked some other girl that my coworkers knew if I could have her Carwoo! sticker and she said “Nope!” REJECTION!

I was so happy! I told her about the challenge and she made me ask her friend out to dinner. Her friend thought about it and then said “I don’t eat dinner”. SILLY REJECTION!


Yesterday I was at Starbucks and their veggie sandwich was literally half the size of the turkey one, so I asked a Starbucks employee if i could have two sandwiches for the price of one. She said no. I decide after this that I’m going to try to avoid business transactions. REJECTION!


I went in for a hug with someone – and she rebuffed this advance. I was a little shocked, but then I realized I had told her about the challenge so it didn’t count. (She then gave me a hug afterward.) SORT OF REJECTION!

Later we were trying to unload our isocket tshirts to people at the conference. Most people were happy to take a shirt, but I approached a few people who had absolutely no interest in a free shirt. REJECTION!


This day was tough. A girl I had met the night before had given me her phone number and told me to call her to get a drink the next day. I didn’t really want to call, but my coworkers said I had to. So I called and left a message and she never responded. SORT OF REJECTION!

Then at the airport I told the TSA people that I had a knee brace before I walked through the detector and it didn’t go off. They said I still had to do a scan. I asked if I could skip it since there was no alarm but they said because I disclosed, they had to. What else would you expect from the TSA? LAME REJECTION!


Was going to ask a girl on the train for her number, but there were a bunch of other people there and I didn’t want to make her feel awkward (aka I was being a wuss). FAILED REJECTION!

Then at lunch I complimented a woman on her sunglasses and asked if we could swap. She refused and said that her sunglasses wouldn’t look good on me. REJECTION!

More interestingly, I then decided I would ask another cute girl on the train for her number. This time, I end up sitting across the aisle from her and had a conversation with her (which was mostly her getting nervous energy out because she had forgotten to validate her caltrain ticket). By the time we got off the train and I went to ask for her number, we had connected enough that she said “Sure!” Not bad at all. FAILED REJECTION!


I wanted to knock my rejection out right away so when I was at the Caltrain station, I was looking for opportunities to get rejected. Then I spied a guy eating a croissant and decided to ask if I could have some. Who gives strangers a piece of their croissant? He kind of looked at me funny and pointed at the coffeeshop where he got it, but I insisted that I wanted a piece of HIS croissant. When he asked “just a little piece?” my heart sank. He ended up giving me his croissant. I had to eat it, smile, and then slowly back away. FAILED REJECTION!

Later in the evening, I was at a bar in SF at a bar – I introduced myself to two guys and they were like “Whoa you’ve changed!” Apparently they had run into another Asian guy named Jason at this bar. So I started joking that we needed to fight until there was only ONE! And I asked one of the guys if he’d be my 2nd. You know, in case I died. He said “Yeah, I don’t think I’m down.” REJECTION!

My non-duel partner friend then said “I’ll think about it though if you introduce me to that cute girl over there.” He pointed at someone. I didn’t know who she or any of the five guys she was talking to were. But I said “Ok” and just walked over there, introduced myself to the group, started talking with the girl. After a second, I asked her “Have you met Eric?” After seeding their conversation with a few hooks I took off and let Cupid do his thing. NOT REJECTION BUT STILL AWESOME!