FAQs

Why did you start doing this?
There were a few reasons.  Mostly, because I had thought of doing something like this for awhile and never really had the courage or motivation to do it.  I finally got a few kicks to the butt and decided to get out there and do it.  Those kicks to the butt were in the form of a few of my close female friends going out of my life for one reason or another.  I also broke up with a girl I was seeing because she was rather selfish and nasty to me.  So, there was a short period of time where the closest non-related women in my life were basically out of my life.  I thought to myself: "I can sit around and be bummed about this, or turn it into motivation."  So, I made that my motivation to get out there and start doing this challenge.

How was it the first time?
It was really nerve-wracking.  I was incredibly nervous the first time.  I was walking around the Super Target in Fitchburg, trying to work up the nerve to talk to someone.  I wanted to leave, but I knew that I would regret it and feel like a failure later if I left without doing it.  Also, I told myself I wasn't going to leave until I did it.  I was over by the children's books, looking at a few Dr. Seuss books, when I saw a woman that looked nice.  I asked her which of the two books would be better to get for my nephew.  At the time, I thought I needed some kind of reason to talk to people.  It's funny looking back on that, because at that time, all I needed to do for the challenge was get someone's name.  Now, that would be incredibly easy to do.  I've also discovered that you don't need a reason to talk to someone.  You can just see someone that looks friendly and talk to them.

Have you ever had any bad reactions?
I guess that really depends on what you mean by bad reaction.  There haven't been any that I've thought were bad.  Nobody seemed to really take offense to it or say anything negative to me.  The worst I usually get is that the person just ejects from the conversation.  There was the one woman that I approached twice, and she asked me about it the second time.  There was also the woman that was really taken aback that I saw again and tried explaining the challenge to her, but she was still taken aback by someone being friendly to her.  That one was really weird.

How many people actually talk to you?
I would say around half the people I approach are willing to have a conversation.  I've met a lot of really friendly people.

Why do you only approach women?
This is a good question, and I'm not entirely sure.  I guess I feel like it would be weird for a guy to approach another guy and just start randomly talking.  It shouldn't be weird, though, and at some point I will probably have a challenge where I approach guys and talk to them.

Why do you still do the challenge if you have a girlfriend?
 Update: I don't have the girlfriend anymore, but I'll leave the initial answer, because it's applicable to any relationship I will be in, in the future.

Because the challenge wasn't about finding a girlfriend.  That wasn't the endgame.  The challenge was about growth and adventure and I'm not done with either of those.  When I met her, I stopped asking for numbers and started talking more about the challenge.  Now, I give out cards with links to this blog and the facebook page for it.  Also, I think this is a great skill I've built, but I feel like I have to keep doing it, or I will lose my nerve. 

Does she know about it?
Yes, obviously, because that's how I met her.  And she thinks its cool.

How many people that you meet do you talk to afterwards?
Sadly, very few.  I have a lot of great conversations and people seem to be really interested in the challenge, but then I never hear from them again.  That's one thing I haven't been able to figure out.  My best theory is that when I approach them, there's a bit of novelty, because that doesn't normally happen.  There's an excitement to the interaction.  Then, once the interaction is over and the excitement has gone down, I'm just some random guy with a website.  I have to build some kind of strong connection with people to give them a strong reason to actually be willing to talk to me after the interaction.  That just doesn't happen that often.  Even the conversations I have that I think "wow, this is a really cool person and I'd love to talk to them again.  They seem like they're really interested in my challenge, which is awesome!"  I don't hear from most of them, either.  If you're reading this and you're one of the people I met, drop me a line.  Even if it's just to tell me some insight about this from the other side of the interaction.

What's the best interaction you've had while doing this?
It's too hard to answer that, because I've had some really good ones.

What's the longest you've talked to someone?
Around 30 minutes, to the woman I met in Barnes & Noble.  It helped that she was already sitting down, so logistics worked out well.

What is the best observation you've made while doing this?
That whole "you can't judge a book by its cover" cliche has some truth to it.  There's been some women I've seen where I thought "she doesn't really look that nice, but whatever, I'll approach anyway." and they led to some of my better conversations.

Has this been worth it?
Yes, absolutely!  My only regret is that I didn't start doing this 10 years ago.  I've noticed quite a change in myself.  I went from someone that was really nervous on my first approach on May 1, to being able to talk to pretty much anyone.  I'm still excited, but it's not really nervousness.  These past few months have been quite the adventure.

Should I do something like this?
Yes.  What reason would you have for not doing it?  If your answer is "nervousness" then ask yourself if that's a good enough reason.  A lot of fun things happen when you step outside your comfort zone.  Fortune favors the bold!

Can I try this with you?
Actually, nobody asks me that, but I would totally go and do this with a person.  In the words of Iceman, "You can be my wingman (or wingwoman) anytime!"