10th of August 2015

Helping Joe, Episode 28 Part 1


In Part 1, Joe goes on two dates in one night and makes a big mistake in how he set these up. Charlie & Nils give Joe advice on how to give himself the space and time to have better dates and when it’s okay to cancel dates. They also talk about bad advice Joe read from a guy who “hacked” online dating.

“Don’t put a ticking clock on things that don’t need one.” – Nils Parker


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This episode is sponsored by Land A Job You Love, a course developed by our own Charlie Hoehn about how to work with great entrepreneurs and startups. Click on the link to receive a big discount on the course as a listener of the podcast.


Joe’s Thoughts and Takeaways From This Episode:

Hey this is a running commentary of random thoughts, notes, and takeaways I had during or after this episode. – Joe

@Beginning – I had 2 dates in 1 night and kind of fucked up

I scheduled them back to back at 7pm and 8pm at locations that were a mile apart from each other. The 1st was at a wine bar and the 2nd was at an ice cream shop.

I was cool for the first date, not self-concious, because I worked out (sprinting) right before + I got there a little late so I wasn’t waiting with nothing but me and my crazy thoughts to keep me occupied. Maybe I should start showing up a little bit late to dates because 1) most girls are 10-15 minutes late anyways and 2) I hate waiting alone by myself. I get too in my head. Working out before dates is easy way to be relaxed during the date.

I was arguing with the girl on date one about something stupid: “Do you generally not trust anybody’s opinion or statement if you don’t already know the fact that they are talking about? How could you know if they are wrong if you don’t know one way or the other?” – Nils

Yea that’s a fair question and I didn’t really have a good answer. In this case, it was a stupid meaningless fact that I just didn’t believe. At least I had fun with it here by making a bet on it to see who was right. I should do this everytime I get the inclination to disprove or argue with someone. Just make bets to see who is right and wrong. And if I lose enough times, keep losing money, maybe I’ll stop doing this.

“It’s potentially a canary in the coal mine if you find yourself not trusting anything she has to say just because you haven’t heard of it before or it sounds crazy. Practice a little benefit of the doubt or trust or faith.” – Nils

“Right or wrong doesn’t matter. What matters is the connection between you and her.” – Nils … And it was silly that I would argue with her about this because it doesn’t matter, like at all. I should have just let it go… “oh that’s weird” and that’s it.

We get back to the small clusterfuck that I created by scheduling these dates too close together. I wish I had stayed there with that first girl. I liked her, the date was going well, I didn’t want to leave. The breakdown of events:

7:45 – Texted 2nd date … I’m going to be late, let’s make it 8:30.
8:30 – rolls around, I still haven’t left wine bar yet. She texts and calls “I’m here!” I ask for the check before girl 1 is done drinking her wine. She drinks it quickly. I feel like a jackass.
I text back “I’m on my way” to 2nd girl.
8:45 – I kiss the girl on first date and walk very quickly towards location of the 2nd date.
I start running & call the girl I was supposed to meet at 8:00. Profusely apologize and tell her I’m on my way. I start sprinting.
9:00 – I finally get to the ice cream place and we start talking, surprisingly, she isn’t pissed.
I felt really bad when I got there and wasn’t sure if she was just going to be pissed and yell, but she was actually really nice about it. I probably would not have been nice about it if I was her. I would have already left by now.

But I wasn’t that worried about it in my head because I had just gone out on a good date and was feeling good from that. And I was kind of thinking how crazy it was just that I was doing this, going out with 2 girls in 1 night. I was so far away from doing something like this or making this kind of mistake when we first started this. It was kind of funny to recognize that. So even if this date went horrible and didn’t last long, I didn’t really care if that happened.

“Did you find her less attractive because she was willing to stick around and wait an hour to meet you.”
– Nils

No, I found her unattractive because she had some annoying ticks or conversation habits that I really didn’t like. And in general I just wasn’t that into her. I didn’t say this on the podcast but towards the end of the date this girl was so bored or out of it or whatever that she started picking ear wax out of her ear, looking at her finger, and discarding whatever she dug up… like a kid would. Kinda gross. I wanted to yell at her “What are you doing?!” but I just said nothing instead.

“Why did you put [the dates] together so close?” – Nils

This was a good question. Part of me was thinking one of them wouldn’t show or that one date wouldn’t go well. Also I just didn’t think about it, was kind of stupid.

Nils mentions that I was applying a speed dating mentality to these dates that are not speed dates. These dates could go anywhere. What if it was great after that hour? I just didn’t think about that. I thought I would know within an hour if I liked her and wanted to see her again and that would be it. Or maybe she wouldn’t show up. I didn’t think about what happened if we really hit it off, which has happened with other dates.

“This strikes me as a version of the attitude early on that was ‘I just go to get through this.’ You put a false ending on something that took the emotion out it.”

@19:00 – “You have the right to postpone or cancel dates.” (My inexperience)

I argued about this, but they pointed out… What’s more rude: Showing up an hour late, wasting someone’s time or texting them an hour before the date to cancel? Yea I should have texted an hour before, fuck. The thought of canceling with the 2nd date just never crossed my mind. I don’t know why. I just felt like I made a commitment and I didn’t want to be a dick and cancel right before. Instead, I was a dick and showed up an hour late. God damn it.

“You don’t owe her anything beyond [a text or call cancelling]. You’ve never met her.” – Nils

Why do I feel like I owe her something?

“I think this might just be inexperience on Joe’s part scheduling multiple social activities… This is an easy thing to fix.” – Charlie

Yea I think he’s right. I hope he’s right. In the past I didn’t have as many social events or dates going on as I do now. So I don’t have much experience cancelling anything because I didn’t have much going on to cancel. I was just clueless and a little frantic that night. I probably ended up pissing off both women. Oh well.

When I tried to make it up to her by paying for dinner: “It’s the please don’t be mad at me thing.” – Nils

Yep… I feel stupid looking back at this, like why should I care if this girl who I don’t even know is mad at me. But it makes sense that I would feel this way given my past history/trauma and all that crap (Episode 24 @15:00)

“If there’s one thing that defines manhood, other than having a penis, it’s [hating to make women cry or have women be mad at them].” – Nils

I’m not quite sure what he meant by this. I wish I had asked him in the moment what he meant here. Is this the cultural trope from sitcoms of angry wives getting mad at stupid husbands (Raymond, King of Queens, any sitcom on right now)?

“You don’t want to put yourself into a position to NOT be able to continue connecting with someone that you like and you don’t owe anybody anything as long as you are respectful and mature. Your responsibility first and foremost needs to be to yourself and then it’s to other people.” – Nils

These are 2 great pieces of advice. I didn’t realize this at the time but by cutting that first date short, I missed out on more fun or a better connection with someone who I liked.

And on the 2nd point he made here, about my responsibility to myself & putting that first, this is a big thing that I took away from reading that No More Mr Nice Guy book. I think his first piece of advice about any relationship is that you have to put yourself (your needs) first. I’ve rarely been like this. I’m always trying to make sure she’s happy or cool, even at the expense of my own happiness, which is fucked up. I think I get this from my dad. He does this a lot with everybody. Another thing to recognize and change about myself.

“Going forward, don’t put a ticking clock on things that don’t need one.” – Nils

I brought up this video I saw of a pickup artist guy who “hacked” online dating and set up 30 minute dates back to back, like speed dating (The video is out there but I won’t link to it because fuck you). At the time I saw this, I thought it was a good idea. But practically, this was a horrible idea and I felt like an asshole doing it. It also probably made the women feel like bad, like they wasted their time with a jerk. You can’t speed-date when only one person is in on it. Nils was right here, that’s fucked up.

@29:00 – Date with the Persian girl I have been seeing.

I think this is my 4th date with her. The 2nd date was the best date ever from a few episodes ago. She’s great, lots of fun. I don’t think I have connected with physically as well as with other girls. When we kiss it feels like something is off sometimes. Maybe we just need to do it more and figure it out. She is really funny, great sense of humor, actually makes really good jokes which is hard to find in a woman, at least for me to find.

We watched Can’t Hardly Wait back at my place. This is a classis HS party movie that I haven’t seen in a long time. So many great characters in this movie.

Earlier on in this series either on the podcast or via text, Nils said that I am a lot like Seth Green’s character in this movie and I thought he was full of it because that guys is crazy. I re-watched the movie and realized yea that’s totally me … his fashion sense + checklists about sex + trying to be cool. It was funny watching this and just


We spend the whole second part of this episode talking about that date.

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