Day 9 – Busy busy but a date

Before I get into the meat of this day, I wanted to say thanks for the support you guys gave me over my last post. Things do get hard and while I do not have any intention of giving up, the temptation is definitely there. I appreciate the kind posts and emails!

Day 9 was OK. Nothing stand outish, but definitely bounced back from yesterday.

Spent a lot of time walking around non dense areas looking for girls to talk to. I need to stick to the dense areas. Though, I really don’t want to run into the same folks too much. I may have to start seeking out new areas soon.

I also had a coffee date today. I feel like it didn’t go that well and this girl wouldn’t want to hang out again. Let me vent a bit about dates.

I’ve definitely felt this way for a while… Like often I’ll go on a date, and it just won’t be super fun. It’ll be awkward. Like, I’ll have boring, factual conversation or I’ll try to relate to a girl “emotionally” and it comes off weird. I’ve done the other end of the spectrum where I’m super aggressive/touchy/kissing early on in the date and that just feels like a bit too much…. Ideally, we’d joke around, flirt, and chat but I find it really difficult to get into that state of mind… especially in the middle of the day or after a hard’s day work.

My dates can sometimes feel like this. It hurts me as much as it hurts you.

My dates can sometimes feel like this. It hurts me as much as it hurts you.

I find the great dates I’ve had (which haven’t been recent) were just easy. I settled on the reason being that the girls just wanted the date to go well and helped keep it flowing. So maybe the girl has to be into me already in order for the date to go (I mean, she’s probably already somewhat into me if she’s meeting up…. but maybe really into me or something). I wonder if this is a cop-out and I need to up my ante on making a date more fun. Maybe I should do something beyond just grabbing drinks/coffee

Note: I don’t do dinner dates until we’re well into a relationship-y phase… for a bunch of reasons – namely they can be awkward, there’s no easy exit if things don’t go well, they’re costly, and spending a bunch of money up front seems to communicate “I want to impress you, please like me”. Hilariously, some female friends I’ve mentioned this to have gotten indignant for my not doing a “proper” dinner first date… I cynically wonder if they’re just mad someone might be threatening their ticket to free fancy meals.

Perhaps if I start doing fun activities (like bowling, pool, or something more active) they’d get better. Perhaps it’s an experience thing and I’ll get better at dates the more I do them. Or maybe I just need to find the right girls…

Then again, I’ve ended up dating girls who I’ve gone out on dates, which I thought were boring… so maybe they don’t need to be fancy.

What do you guys do on dates to make them fun, not stuff?


  • 5 approaches (normally wouldn’t count this day, but the date probably would have been another 5 or so)
  • 1 to follow up on
  • 1 date


  • Stay in more dense areas
  • I wonder if there’s a way to have more fun on dates instead of being super stiff


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7 Responses to Day 9 – Busy busy but a date

  1. Mitch says:

    Take a walk around an area of interest. The slow constant change of scenery provides lots to talk about.

  2. queenie says:

    Nothing wrong with approaching lots and lots of people, but basing the entire thing on appearance seems wrong to me. Is there nowhere that you are likely to find women who are into the same stuff you are? Music, wine, excellent coffee, baseball…something? Seems like a common interest might be a good jumping-off place for dating conversation too.

    • This is a great point (and why I said earlier that I suspect fun events like random festivals, etc might be the best way). The challenges are:
      1) I need a LOT of people (the whole point is doing this in a month and increasing effort leading to success). Filtering by interest and maintaing quantity is tough, but the streets have a ton of people.
      2) Looks are important to me! I think it’s a necessary but not sufficient condition…

      Maybe I’m just atypically shallow, but I don’t think I’ve ever had a girl, whom I wasn’t initially physically attracted to, become substantially more attractive due to personality, etc. I HAVE come to love girls whom I dug physically but suspected had a bland personality at first though… Based on the other guys, random articles I’ve read, etc. this sounds consistent like a consistent male thing… It sounds like females work the other way around though (thankfully!).

      • queenie says:

        OK sure, looks are good. But…really? That’s the most important thing? OTOH I certainly get the thing where you are going for numbers. I just think that you could skew your numbers by searching in a place where compatible women are likely to be. Also, if you are having fun, you will seem more confident and fun and will (I believe) therefore be more attractive.

      • … I am a dude. Looks are very important to dudes (why do you think women put so much effort into looking pretty?). Probably the most important factor. Many guys won’t admit this since it’s societally frowned upon or they’re trying to pander to women who might resent the notion. Fuck that.

        I push back! These places that are more likely to have compatible women still pale in comparison to the raw numbers game of the street.

        Let’s say I’m compatible with 5% of women in general. In the street, I pass by thousands of women in a given day… I’ve done about 20 approaches a day (of this random sample of thousands, I’m sufficiently attracted to 20 – that’s like 2% rate or less). So of the 20 I approach, 1 will be compatible. Just need to have each other realize that and we’re home free.

        Let’s say I go to a super fun guitar playing event or math blogger event or something… A very big event will have hundreds of people. Halfish of them will be women (probably the stuff I’m interested in will have more guys… because I am a guy… and like guy stuff). So let’s call it 100 women (big ass event!). Since this is an event where I have a common interest, let’s say there’s a 30% chance of compatibility (very high!). Now given my 2% approach rate (girls at events I’m into will probably be less attractive than a random sampling, but let’s ignore that), I’ll be sufficiently into 2 girls… I do have a higher chance of being compatible with each two, but my expected returns is 0.6 almost half as much as the other method….

        Agreed about the having fun point!

        I’m sticking to street because if I can crack it then it’d be awesome!

  3. Bryan says:

    A couple things.
    If you feel like you’re wasting a lot of time walking around looking for girls, perhaps it would be worth trying just plopping yourself down in a stream of attractive women. The equivalent of just setting up shop around Newbury St or the Prudential mall and then pulling the fish off the stream when they come by. It’s what bears do.

    I think prescreening for common interests by going to a lot of wine tastings or pokemon card auctions or what-have-you is generally a good practice but probably better suited for a general lifestyle practice more than it is for The Girlfriend Hypothesis Project. I don’t think you’ll get as much throughput this way, and my bet is whatever the common interest is, it is virtually irrelevant for your guys’ compatibility. Great dating is about great chemistry, which may not be really correlated with demographics like “likes wine” or “likes clubbing (baby seals)”, etc. In my experience, commonalities like this are useful for initiating conversations, but really don’t matter much for maintaining any kind of relationship.

    On dates. I’ve had some success doing some wacky stuff like starting with a quick cup of coffee and then conning the girl to come shopping with me, something I had to do anyway. Movement is really helpful and puts you in a context that is more integrated in the girl’s life than simply that single instance at the coffee shop. Moving around also provides a constant stream of new things to talk about, effortlessly, and allows you (and her) to see how she (you) interacts with the rest of the world, which can be huge turn ons or offs, depending on who they are.

    Also, I hear AA is a good place to pick up chicks 😉

    • Good points!

      For walking around, I have actually been sticking to densely populated regions and just walking around in them. Sitting still is a little weird for me… I’d like things to be as spontaneous as possible (strange, I know given I’m trying to repeat the same thing over and over). I also fear that sitting somewhere and doing this over and over might attract a lot of attention which I’d prefer to avoid.

      I hear you on the common interests thing. I’m not sure why it’s been so good for me in the past… Maybe it just relaxes the girl and makes her feel like she’s meeting a guy through a more acceptable method… Though who doesn’t want a romcom meet? Watch more Reese Witherspoon, ladies!

      Moving around is tough in the winter since, as we’ve discovered time and time again, women don’t like the snow. Still, your point is taken – maybe a nice mall or something. I actually find alcohol is a really must have… Not in the creepy, I want to sleep with you way, but rather in the it relaxes the nerves, makes joking easier, and lends itself to fun.

      I do think moving to multiple bars is a good idea since it mixes the two ideas… Also, maybe will revive some old fun dates that worked great when I lived in cities I knew better.

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