Update

I haven't written anything in the past few days because I haven't really done any approaches in the past few days.  Thursday and Friday I was feeling a bit under the weather, so I didn't bother approaching.  It didn't help that I was on-call  for work and thus didn't go out much.

I must say, though, that I have lost interest in doing the challenge somewhat.  I don't know what it is, but it feels contrived or like my heart isn't in it.  And a lot of the thrill is gone, because it's not really a challenge anymore.  The only challenge is logistics: finding time to try to approach and finding someone I want to approach.

Initially, I thought September was going to be a fun month.  I had plans of using song titles as opening lines and thought that would be really fun.  Then, I got in a relationship and that threw the challenge in a flux.  I still did the challenge, but I thought I would feel weird about approaching women that way while being in a relationship.  So, I kept it neutral.  If I had a good conversation with a woman, I wouldn't ask her for her number, instead I would give her one of my cards that has a link to this site and my facebook page.  Of course, that means never hearing from them again, because I don't think any of the people I give my card to actually look at this blog.  I've given this blog to people I know that haven't even read it, so why would a stranger?

I thought there was something really worthwhile in this challenge, that's one of the things that drove me at the start when I was really nervous talking to people.  I thought that when I told people about it, they would share that excitement and it would be cool.  However, I've found that few people actually really think it's cool.  And I don't even hear from those people again.

In order to get the challenge back on track and actually make it a challenge again, there are two ways I could go with this: approaching multiple women at a time, and approaching guys.  With multiple women, I've avoided that, because it just seems easier and maybe more authentic if it's a one-on-one interaction.  With approaching men, I guess there's a part of me that thinks it's weird for men to approach men like that, even if it is neutral.  Inevitably, though, I know I'm going to have to go there, in the interest of personal evolution.

I haven't given up on the challenge, I just had to really think about where it's going.  I know I can get it back on track.  I will come up with something for October that will be fun and challenging.  If you've gotten this far and you want to help, either leave a comment or email me with ideas. 

Thank you!


Will

September 26, 2013

So I have to admit that I had started to let my recent run of unfriendly people rain on my parade a little bit.  I was slowly losing interest in my challenge.  However, I decided to persist.  Today, I met a woman that was really friendly.  I found out that she just recently moved to town for a job as a statistician.  She also likes running and biking, which I can appreciate.  It was a really nice conversation, which definitely reignited my interest in my challenge. 

It just further points out that if you don't give up, you never know what will be just around the corner.

September 25, 2013

While I was at HyVee yesterday, I passed by a woman and we exchanged smiles.  I saw her again later on and commented that she had a nice smile.  I introduced myself, but the conversation didn't really go anywhere.  At least she was nice.

September 24, 2013

I saw a woman at HyVee that looked interesting, so I went and talked to her.  I introduced myself and asked her for her name.  Then I asked her what she does and she mumbled something that I couldn't understand and walked away.  As she was walking away, I said "OK...."

September 23, 2013

I am on-call this week, so I didn't have much time to try to approach.  I saw a woman in HyVee and talked to her very briefly.  I found out that she's from Indonesia.  I was in a bit of a hurry, because I wanted to get in a run tonight, so the conversation was very brief.  At least she was nice.

September 21, 2013

Today I talked to a woman at HyVee.  I found out that she works at a restaurant.  We talked about that, and how it offers her the opportunity to meet a lot of new people.  I talked about the challenge that I'm doing, and she thought it was a cool idea.  We talked about how it shouldn't be weird to just be friendly to people that you see in the grocery store.  She was a very friendly person and I feel like after my rut of rude people, I'm on a trend of friendly ones.  Hurray!

September 20, 2013

 This one is a little late.  Sorry about that!

I talked to a woman in Metcalfes @ West Towne.  I found out that she's a student, close to getting her bachelor's degree.  I told her about my challenge and my blog, and offered to give her one of my cards that has the link to my blog.  She declined, saying she's not really into blogs.  At the time I thought that was rude, but when I thought about it, I guess it's better than the people that take my card and never actually look at my site.  At least she was honest.

September 19, 2013

There's nothing to report from yesterday.  I was feeling under the weather and didn't really get a chance to get out and try to approach.  I got back into the swing of things today, though.

On the way home from work I stopped off at Metcalfe's to get something to eat for dinner.  It started storming while I was there.  I saw a woman that looked nice, so I figured I would talk to her and maybe pass enough time for the rain to stop.  I found that she was really friendly, which was nice, considering my experiences as of late.  She told me that she works in accounting, and I asked how she got into that.  Then she asked what I did, so I told her.  We talked for a little bit, then I told her about my challenge.  She thought it was a cool idea.

It was nice to actually have a decent conversation for a change.  All the ones lately have been really short, so this was nice.

September 17, 2013

It was nice to talk to someone that was friendly for a change!  I talked to a woman in Metcalfes at West Towne and she was actually really friendly.  It was a breath of fresh air.  It just goes to show you, though, that even when things aren't going your way, you never know what's around the next corner.

I asked her about what she did and then told her about my challenge.  It was a nice conversation for a few minutes there.  Definitely what I needed after a string of not so great conversations.

September 16, 2013

I almost didn't approach anyone today.  I stopped off at Metcalfes and Barnes & Noble at West Towne, but there were no good opportunities.  Which, was too bad, because I was wearing my suit to work today.

So, I thought, this might be the day I break my streak.  However, after running tonight, I had dinner then went to HyVee to get some food for the next few days.  I decided to keep the streak going, so I said hello to a woman that I was on the same aisle as.  She was looking at tea, so we talked about tea. I told her I had been to a nice tea place on Friday night with my girlfriend.

That was pretty much all of the conversation.

September 15, 2013

I approached a woman in HyVee and said she looked friendly.  I introduced myself.  Then, I asked her what she did and she said that she was actually busy, but thanks for saying hello.

I'm on quite a run now where conversations don't last even a minute.  In fact, I think my last good conversation was with the older gentleman in the Florida State shirt.  I wonder if part of the reason is that I'm not as enthusiastic about doing this anymore and somehow that's carrying over into how I'm approaching people and they pick up on that.

September 14, 2013

I introduced myself to a woman at Walmart.  I found out that she's studying for a phd in economics.  Thankfully, unlike the last few people I had talked to, she was actually nice.

There's not much to write about this one, as it was a very short interaction.

September 13, 2013

I approached a woman in Metcalfe's at West Towne.  I said she looked like a nice person,so I thought I would introduce myself.  I asked her what she does, and she said she didn't have time, she was busy.  Then she walked away. 

I'm stuck in a bit of a run of really rude people.  That's how things go sometimes, though.

September 12, 2013

I approached a woman at Barnes and Noble.  I went up to her and said "Hi, I don't think we've met, I'm Will."  She kinda looked at me funny and said "hi."  I said, "oh, sorry if that was weird, I just like talking to people and being friendly.  What's your name?"  She told me her name, then I asked her what she did.  She said "I really just want to read this book."  I saw that it was a wedding book, so I asked "oh, are you planning a wedding?"  Her: "Yeah, it's for a friend."  Me: "That's cool, when are they getting married."  At this point, she just ignored me, so I waited a few seconds, then said "Ok." and walked away.  I was really struck at how rude this woman was to someone that was trying to be friendly.

I feel like you can tell a lot about a person by how they treat random strangers.  It's not someone that is in your life and that can do things for you, so kindness is truly an act of altruism (well, not entirely, because pure altruism is rare, but that's another topic.)  I think people that treat strangers poorly, even if they are kind to the people in their lives, that says something about them.  Somewhere, deep down, they are not as nice as they appear.

And you might retort by saying "yeah, well she said she just wanted to read the book and you kept talking to her!"  True, but it's not like she was sitting somewhere reading, so was standing in the aisle.  Also, during our conversation, she put the book back on the shelf.  Regardless, that's no excuse to be rude to someone.

September 11, 2013

Today I approached a woman in Metcalfe's at West Towne.  I said that she looked nice and introduced myself.  She asked me why I was doing that.  I told her that it's something that I do, that I set a challenge for myself to talk to at least one random person a day.  She said "oh, so I'm the lucky one?"  I said "yeah, you looked like a friendly person, so I thought I would talk to you.  I'm sorry, I didn't get your name."  Her: "oh, I'm not telling you my name."  Me: "Okay"  and then she walked away.

September 10, 2013

I approached an older gentleman at Metcalfe's at West Towne.  He was wearing a Florida State shirt, so I asked him about it.  I found out that his daughter was a student there and now she lives up here with her husband and their child.  He still lives in Florida, but came up here to visit.

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!"

September 9, 2013

I went for a run tonight, so I didn't have much time between work and the run to approach people.

I walked around Metcalfes @ West Towne for a bit, but didn't see anyone to approach and was running out of time.  I almost bumped into this woman, so I introduced myself to her, then told her about the challenge.  I told her that early, because it was a good way to keep the conversation short, as I needed to get home and get ready to run.

September 8, 2013

Today, I also didn't spend much time trying to approach people, because I had other stuff going on.  However, while getting some food for the next few days at HyVee, I saw a woman that looked friendly, so I talked to her.  I found out that she's in school to get a PhD in environmental science.  I told her about my challenge and we talked about that for awhile.  She seemed really interested in it, which was cool, because I love sharing with people that are genuinely interested in what I'm doing.  Throughout the whole conversation, she was very friendly.  I'm glad I talked to her.

September 7, 2013

I didn't really spend much time trying to approach people, because I was watching Miami beat Florida and hanging out with a few people I already know. 

I met up with a friend at the Starbucks in Greenway Station.  I then decided to go over to Michaels, to see if I could find a better way to hang up my "The Endless Summer" poster.  I had been hanging it up using sticky-tack, but that wasn't working so well.  They were selling poster frames on clearance for $6.00, so I got one.  While in the store, I was on the same aisle as this nice-looking woman, so I started a conversation with her.  I found out she's a preschool teacher and has kids of her own.  When she shifted her hands (she was holding a basket and I couldn't see her left hand) I noticed she had a wedding ring.  I didn't want her to think I was trying to pick her up or anything, so I told her about the challenge.  She thought that was a pretty cool idea.

September 6, 2013

I had an interesting time in Metcalfe's @ West Towne today when I stopped there on the way home from work.  I ran into a coworker in there and started talking to her.  I was telling her the story of how I met the ladyfriend while we walked around and shopped.  Well, she was shopping.  I tried to get her to do the challenge with me, but she didn't want do, even though she cleverly noticed that as a team we could be called Will and Grace.  I saw a woman that we could approach in the produce section, but she had to get going.  So, we said goodbye and I went to approach the woman on my own.

I introduced myself and asked her what she did.  I found out that she works in investments.  I also found out that she studied psychology, which was interesting, because I studied both math and psychology in college.  We talked about her hobbies.  She asked me if I was new in town and I said "why do you ask, because I came up to you and started talking to you like this?"  She said yeah, and I told her about my 30-day challenges.  I gave her my card so that she could check out my blog.  I'm glad I talked to her, she was a really friendly person.

September 5, 2013

Three approaches to write about today:

The first one was on the way home from work, when I stopped in Metcalfe's @ West Towne.  I talked to this nice woman for a few minutes about what she does for work and for fun.  I told her about my challenge, and she seemed to think it was a cool idea.

The second approach was kind of an accidental approach.  I was standing around at the Arboretum after a run and this woman was walking through the parking lot and I said hello and asked how she was doing.  She asked if we were a run gang, and we started talking about running.  I told her about the group and that we have a group for beginners that has just started up.  I gave her my run group card and she told me how serendipitous this was, which has been a general theme for her lately.  At one point she remarked how funny it was to just talk to a random stranger and then that kind of connection happens and I said "well, talking to strangers is kinda what I do."  Then, I told her about my challenge.  She thought it was pretty cool, so I gave her my card for that as well. 

The last approach was when I stopped at HyVee after the run to get some food for tomorrow.  I wasn't really planning on approaching anyone, since it was late and usually there's not many people in the store that late.  As I was about to walk down an aisle, I saw a woman there and decided to talk to her.  She looked friendly enough, so why not.  I found out she's studying to be a teacher, so we talked about that for awhile, since as you might remember, I used to be a teacher.  Then we talked for a bit about hobbies.  I found out that she cross country skis and she's a runner, which I can certainly appreciate.  I told her about the challenge and she really seemed to like the idea.

All-in-all this was a great day for challenges.  I met three really friendly people, which is always nice.

September 4, 2013

Only one approach today as well.  I haven't dedicated much time to it this week.

Tonight, I was going to go for a run with a group, but I showed up 30 minutes early for the run (which was on the UW campus) so I decided to walk around a bit and kill some time.  I ran into this nice young woman as I was walking back.  She's a sophomore from Hawaii.  She was incredibly friendly, one of the friendliest people I've met.  It was like she had no problem with a random person coming up to her and talking to her, like it was normal.  Which, I really feel like it should be normal for two strangers to just start talking to each other.  So, kudos to her for that. 

I told her about the challenge and we talked about that.  We also talked about what she's studying and what it was like moving from some place warm to some place with cold winters, since I can relate to that.  It was a great conversation.  I'm glad I was early and had time to walk around.

September 3, 2013

Not much to report today, just one approach.

I stopped off at Metcalfe's at West Towne on the way home and approached this one woman and said she looked nice.  I introduced myself, but she said she was busy.  I said "oh, I'm just doing a thing where I try to meet at least one random person per day, so if I see someone that looks nice, I talk to them."  She said "oh, that's cool, well good luck with that."

I don't know what it is, either I'm just running into a string of bad luck, or my heart hasn't really been in it lately and that's coming through when I talk to people.

September 2, 2013

Just one approach today.  I saw a woman in HyVee and introduced myself, but she said she was in a hurry.  I said, "oh, okay, I'm just meeting people" and she at least stopped to listen to me tell her briefly about my challenges.  I thought that was cool.  It made me think that she was being honest about being in a hurry.

September 1, 2013

I did two approaches today.  The first one was a woman that was giving away samples of apple cider in Metcalfes @ West Towne.  I talked to her for a little bit.  Not a great approach, but today was just a bad day for approaching for some reason.  Sometimes that just happens.  I was in several stores today and really didn't see any good approach opportunities.

The second approach was while walking outside at Hilldale.  There was a woman sitting on a bench playing with her phone, so I stopped and talked to her.  The whole time during the conversation, she never looked up from her phone.  I thought that was rather rude, so I didn't really bother talking with her much.