Upstart's Progress Log - I'm Gonna Quit My Day Job ONCE & FOR ALL.

[Squilliam]

Uhh, restaurant (I didn't say dishwasher) . But only for a little while longer, soon I'll have my art career off and running, haha.

Oh, does your industry make a lot of money?
Not really, unless you're really good (like me) I had to resist the urge to pull out my instagram to prove myself.

I keep getting into this dynamic with older ladies it's like they have all the expectations I can't meet because I'm fucking broke.

I just have this discomfort around being so poor, I'm literally below the poverty line. I don't even know how I'm surviving off of negative money at the moment. Payment plans, and recurring bills I guess. Always teetering on the edge of financial ruin, again.

When she mentioned that for next date we should go on a glass bottom boat ride, I had a mini panic attack.
I can barely afford to EAT right now, betch!

EE women are generally pretty strong framed. My ex was EE (well, 2nd gen tho) and honestly it was a lot to handle. Those women typically have a very rigid standard of masculinity, they want you to be dominant, to provide, to lead, etc.

Older women are generally less gamey but in other ways they can be more demanding. Older women are more likely to want something serious and settle down.

One thing I learned from my ex is, in EE culture, there's no such thing as "seeing each other". You're either dating, or you're not. Hence why I think you might struggle to have casual sex with a woman like this.

I would proceed with caution. She might not put out next time or the time after that. And in my opinion you shouldn't be ramping up the date quality if she doesn't.

 

[Upstart]

Thanks Bman!

What was your game plan with this date?

Basically, this was just a "get to know her" date. I try to follow the Caleb Jones model where it's second date sex, I don't want to pull on the first date (unless it's on the table) because I want to be able to retain the girl for longer. And I don't want to catch a surprise STD.

Why are you doing dates all the way up north? Did you choose the place or did she?

I chose a spot closer to her to make it more convenient for her in this particular case.
I keep matching with far away girls, but that's how I set up my apps. I usually run out of options near me.

I don't feel like I have the optionality yet to confidently start making girls come up to me, but I know my FWB would make the hr drive from her spot, just because I smash her like no other, lol.

No, cold approach in Austin.

I always though there was an abundance out there. Just depends on the time of day in my case.

And yeah, the broke thing is definitely mostly in my head, but still!

 

[Upstart]

EE women are generally pretty strong framed. My ex was EE (well, 2nd gen tho) and honestly it was a lot to handle. Those women typically have a very rigid standard of masculinity, they want you to be dominant, to provide, to lead, etc.

Older women are generally less gamey but in other ways they can be more demanding. Older women are more likely to want something serious and settle down.

One thing I learned from my ex is, in EE culture, there's no such thing as "seeing each other". You're either dating, or you're not. Hence why I think you might struggle to have casual sex with a woman like this.

I would proceed with caution. She might not put out next time or the time after that. And in my opinion you shouldn't be ramping up the date quality if she doesn't.

Thanks Squilliam!

I'm trying Andy's honesty stuff and just try asking her if she down. Here was my last text to her this morning:
Usually she'll get back to me that night or the next. We'll see wassup soon enough!

 

[Upstart]

4/24/25
JUST WENT ON A DATE WITH A CHILDHOOD FRIEND
What is this, an anime?!

DATE FIT:

Made sure to do extra pushups just in case.

The date was smooth sailing.
She had grown and I had grown, and I said "You sound like an adult now!" We laughed and mentioned Rugrats all grown up.

We had ice cream and we basically talked about our middle school days and what we'd been up to since. She'd been traveling the world A LOT. She keeps very busy and saved up a lot to be able to travel.

Toward the end, when we were sitting, just looking at the lake, I asked her about her dating goals, and she told me, since she was traveling a lot she wasn't trying to stay in one place for too long. I told her I wasn't looking for anything serious, but I'm not the one night stand type. I said I like to get to know a person first before we get physical.

We converse a little more before I say, "Would you be open to a kiss?"
She laughed and said, "Yes, I think I would."

BUT!
When I started to go for it, she said she wasn't ready for anything sexual in the near future.

I said "I thought as much, because that's where I'd take it if we kissed. We'd do much more naughty things later on for sure. Not tonight, but definitely later. "

I also said it was hard enough just to get her out on this date (it took 3 weeks) because she had such a busy schedule. That it would drive me insane just to try to coordinate this regularly.

We laugh.
Then I walk her back to her car, not feeling the slightest bit rejected. We hug for real, and hold it for longer than normal.

I say "it was really good seeing a familiar face again." We commented on how we changed and how we stayed the same, then said our goodbyes.

That was it. I feel like I brought my best self to the date. Carried myself as a man. She appreciated it, but it just wasn't a good fit for either of us.

ONWARDS!

 

[Upstart]

SHE BOUGHT ME THE SHEETS, YALL!​

Friday, April 25th, 2025

I was FLABBERGASTED when I walked into her place the other day. The sheets she mentioned in her delirium were just sitting there on the counter.
We met up again two weeks after that encounter, so I was surprised she remembered.

She made me dinner because I said I was saving cash.
It was fucking delicious rice and stew. I drew a picture of her while I waited.


Andy recommended I start doing this on first dates, so I thought I'd give it a shot today as a thank you to her.

We watched the PJs then got to bed.

Notable moments:​

I FINALLY made her cum just from dick. I didn't think it was possible because I thought she needed a LOT of pressure to be able to cum, but not this time. All I did was swirl my dick around inside using a motion I learned from youtube. Instead of the constant jabbing we usually do, she did not expect this motion.

I was surprised I stayed hard the whole time.
Especially because I had to wear condoms because she was on her period.

I called the night early after we had dinner because I was dead tired and I knew I would rock her in the morning.

Morning came, we got to business.

I brought a mirror into her room to try some shit I read online.
But I wasn't sure what I was doing so I left it alone.

She bent down to suck my dick. Then we did some more stuff on the bed.

Her favorite thing is my fingers, which is basically the main event. I finger her with my left, which is what I usually start with. I touch her new spot again.

Then I really went in with my right when my left was tired. I blasted her with constant vigorous motion until she released EVERYTHING.

All her pent up frustration for the week exploded out. Ironically, there was no squirt.

She was writhing all over, grabbing her sheets, kicking her pillows off the bed while I stood back satisfied with my handiwork.

She nearly fell HEAD FIRST off the bed, lost in pleasureland. I caught her and said "I got you, I got you." and put her back on safely. She was at a complete loss of words. I should record it next time tbh.
Then she said,
"I get paid next week, you want half my paycheck? It's yours."

I just laughed and sucked on her titties as she slowly came back to her senses.
"I could see colors this time, all kinds. In a big swirl."

"Like a galaxy?" I asked.
"No, more like...a waterfall"

Damn, I wish I could nut like that too, lol.

She said, "I look forward to seeing you every week because I know you'll relieve ALL my stress from work."

Then I jerked myself to completion partially in her mouth, then the rest on her stomach, she says next time she wants it on her face.

Afterwards, I washed the dried period blood from my hands.

I said, "let me wash the blood of Jesus off my hands".
She died laughing.

After her shower she made me a VERY good breakfast. Her mom called and she said "sshhhh, it's my mom!"
I'm really glad this is still casual. And we both know it!
She sneezed and I accidentally said "Bless you"
Luckily my cover wasn't blown.

After breakfast, I was in no more mood for sex or even kissing, so she just cuddled and kissed me while I watched Abbot elementary. We stayed like that for 3 EPISODES, before I left.

She takes a real long time to say goodbye.

As a side note, this was my second 3 date week ever.

Russian lady on monday.
Childhood friend on Thursday.
FWB on Friday.

 

[Upstart]

3 APPROACHES OVER 2 DAYS

I skated on my college campus after work. I noticed this girl in blue tights and a massive thigh gap. I was super curious about it, so I decided to catch up to her and ask. I maintained a safe distance gave her some context to my weird question, I was smiling and laughing then said, "does anyone comment on your thigh gap?"

She immediately turned away looking like and kept walking.
I jokingly said "NOOOOOO, wait!" And kept walking with her for a bit to try to explain my line of thinking.
She jokingly said "Nope! Uh-uh. too weird. Have a good day."
I was still laughing when I gave up and said, "Dang, alright you have a good one too. hahaha"

I did feel a little weird for the rest of my time out there and psyched myself out to approach anyone else, but I'm glad I asked, because I was nervous to approach at first. Maybe girls are self conscious about that kind of thing, or it was too sexual right off the bat? I gave myself grace for my austistically honest question.

YESTERDAY
I approached a woman and told her she looked like one of the characters in my comic and showed her the art. She thought it was cute. I asked her if she was single, she said yes, but she was not interested in hookups.

I asked, what she is interested in. More long term or marriage? She said yes. Then I told her "That's cool, I'm looking for something more casual, but I'm glad I met you for a bit"
She said "Thank you for coming up to me!"
I said no problem, we shook hands again and she locked eyes with me. Even when I tried to finish the handshake she took a step forward like she really wanted something more. I smiled and left.

I approached another woman in the same grocery store and asked her about her tattoos, she also said she was single, but wasn't looking for anything at the moment. I said, no problem, just take it as a compliment and have a nice day.

These approaches make up to 65 lifetime serious approaches (thereabouts.)

 

[Manganiello]

She jokingly said "Nope! Uh-uh. too weird. Have a good day."

Lean into that dude. Fuck what they think.

Be out there for what you want.

You should be doing 65 a week.

Honestly the first 7ish approaches each day are throwaways becuase you need to warm up.

Honest to god man, you're not doing enough. You;re more than capable of hitting 70 approaches.

And when you get good, those 70 will give you a decent stream of dates.

 

[Upstart]

YESTERDAY: 5/6/25​

Went out to approach.

Basically went with the social momentum method of talking to everybody. When I have trouble getting out of my head, I always use Andy's mini AA program. REALLY helps.

I smiled at one girl.
Then smiled and said hello to an older lady
Then I stopped a girl who had a cool shirt on and we had a short convo about it. Positive interaction.
Then I skated for a bit, saw a cool looking girl with red hair walking, tried to catch up as she went into a dining hall. Tried to keep following, until I chickened out a lost sight of her. Womp womp.

Then I asked an older man for directions to the library. He pointed it out.
I saw a suuuper cute girl walking away from the library. I passed her, then did a U turn to catch up.
Then she got on the phone.
SHIT.
I kept following her looking for an opening. My mouth was getting dryer as seconds stretched into minutes of following nearby. But it seemed like her convo was light, nothing serious, so I thought:

"Why not give her a fun story for her friend?"

So I walked next to her and put my hand up so she would see me, then said, "you got a minute? "
She said "yeah sure"
Then I said "you look really cute today."
Thank you! she said

we kept walking and I asked her about classes and her final tests. She said she should be fine as long as they grade on a curve lol.

I asked if she was single or looking,
"I have a boyfriend" she said with a smile.
DANG! I said in my laughing exasperated tone.
No worries, have a nice day!
It was nice meeting you! She said.
Oh yeah! i said, and walked off.

Most days I go out, I don't expect approach anyone, feel bad, and go home, but so far, I've been able to at LEAST approach 1 girl per day. A month ago, I wouldn't have dared to approach anyone on campus. I've always wanted to approach waaay more per day, but I'll work up to it.

Just have to remember. "Women aren't my enemy , women aren't my enemy."

TODAY 5/7/25
​

Approached on campus today, didn't have a lot of time so I wanted to make it quick.

I skated past a girl on a bench who had a nice dress.
I went 20ft then 30 ft away , then turned back thinking,
"how can I make her day?"
It was too good an opportunity to pass up.

I walked up and waved as she noticed me. I said hello, then froze for a second. Then said I think your dress is really beautiful.

She said, thank you and I immediately noticed an accent. She said she was going to the library. Had a neutral polite expression the entire convo. I told her she sounded argentinian/spanish, she said she was Portuguese/french, I said "Wow that's cool"

When I asked if she was single, she said she was had a partner. I said, no worries, then we formally introduced our names before parting ways positively.

I had extra confidence from starting early.

BUT there were very few students on campus today. most were finishing classes. I talked to another girl who was wearing long sleeves on a hot day.

I said aren't you hot out here?!
And she said she was wearing it for a business class presentation and it was the most professional clothing she had.
We had a short lively convo about her class, before I fist bumped her and wished her a good day.

I chose not to make that one an approach, but it was a nice interaction.

I did pass by some even cuter girls on the way home but since I was strapped for time i gave myself an excuse not to approach lol. I might have worked up the courage and turned back around if I had more time though!

MY JOB CLOSES FOR SUMMER TOMORROW!​

I don't plan on going back. I've joined Andy's coaching program, so I'm hoping they can show me a way that I'll never have to go back. And how to accomplish all my crazy sex goals as well.

I'm getting paid to work on my own comic book, so I'll be using that and other methods as my ticket out of my day job forever.

Lean into that dude. Fuck what they think.

Be out there for what you want.

You should be doing 65 a week.

Honestly the first 7ish approaches each day are throwaways becuase you need to warm up.

Thanks Mang!

Honestly, I finally just worked up the courage to get to 1 per day consistently. But my job goes on break tomorrow which should give me more time soon.
Where are you approaching that you can find a lot of volume per day?

 

[Manganiello]

YESTERDAY: 5/6/25​

Went out to approach.

Basically went with the social momentum method of talking to everybody. When I have trouble getting out of my head, I always use Andy's mini AA program. REALLY helps.

I smiled at one girl.
Then smiled and said hello to an older lady
Then I stopped a girl who had a cool shirt on and we had a short convo about it. Positive interaction.
Then I skated for a bit, saw a cool looking girl with red hair walking, tried to catch up as she went into a dining hall. Tried to keep following, until I chickened out a lost sight of her. Womp womp.

Then I asked an older man for directions to the library. He pointed it out.
I saw a suuuper cute girl walking away from the library. I passed her, then did a U turn to catch up.
Then she got on the phone.
SHIT.
I kept following her looking for an opening. My mouth was getting dryer as seconds stretched into minutes of following nearby. But it seemed like her convo was light, nothing serious, so I thought:

"Why not give her a fun story for her friend?"

So I walked next to her and put my hand up so she would see me, then said, "you got a minute? "
She said "yeah sure"
Then I said "you look really cute today."
Thank you! she said

we kept walking and I asked her about classes and her final tests. She said she should be fine as long as they grade on a curve lol.

I asked if she was single or looking,
"I have a boyfriend" she said with a smile.
DANG! I said in my laughing exasperated tone.
No worries, have a nice day!
It was nice meeting you! She said.
Oh yeah! i said, and walked off.

Most days I go out, I don't expect approach anyone, feel bad, and go home, but so far, I've been able to at LEAST approach 1 girl per day. A month ago, I wouldn't have dared to approach anyone on campus. I've always wanted to approach waaay more per day, but I'll work up to it.

Just have to remember. "Women aren't my enemy , women aren't my enemy."

​

TODAY 5/7/25​

​

Approached on campus today, didn't have a lot of time so I wanted to make it quick.

I skated past a girl on a bench who had a nice dress.
I went 20ft then 30 ft away , then turned back thinking,
"how can I make her day?"
It was too good an opportunity to pass up.

I walked up and waved as she noticed me. I said hello, then froze for a second. Then said I think your dress is really beautiful.

She said, thank you and I immediately noticed an accent. She said she was going to the library. Had a neutral polite expression the entire convo. I told her she sounded argentinian/spanish, she said she was Portuguese/french, I said "Wow that's cool"

When I asked if she was single, she said she was had a partner. I said, no worries, then we formally introduced our names before parting ways positively.

I had extra confidence from starting early.

BUT there were very few students on campus today. most were finishing classes. I talked to another girl who was wearing long sleeves on a hot day.

I said aren't you hot out here?!
And she said she was wearing it for a business class presentation and it was the most professional clothing she had.
We had a short lively convo about her class, before I fist bumped her and wished her a good day.

I chose not to make that one an approach, but it was a nice interaction.

I did pass by some even cuter girls on the way home but since I was strapped for time i gave myself an excuse not to approach lol. I might have worked up the courage and turned back around if I had more time though!

​

MY JOB CLOSES FOR SUMMER TOMORROW!​

I don't plan on going back. I've joined Andy's coaching program, so I'm hoping they can show me a way that I'll never have to go back. And how to accomplish all my crazy sex goals as well.

I'm getting paid to work on my own comic book, so I'll be using that and other methods as my ticket out of my day job forever.


Thanks Mang!

Honestly, I finally just worked up the courage to get to 1 per day consistently. But my job goes on break tomorrow which should give me more time soon.
Where are you approaching that you can find a lot of volume per day?

Ya my city was quite dead honestly.

So I would just hit 2-3 malls.
But after awhile I just stuck with 2 malls. I would drive to the other once I cleared one.

Would usually hit 2-4 in one mall, and then the other mall was much better could usually do 8 an hour there.

There was a lot time of time spent walking around and finding girls.

It was my most important goal so I'd spend 3 hours on it. Daily.

 

[Upstart]

Ya my city was quite dead honestly.

So I would just hit 2-3 malls.
But after awhile I just stuck with 2 malls. I would drive to the other once I cleared one.

Would usually hit 2-4 in one mall, and then the other mall was much better could usually do 8 an hour there.

There was a lot time of time spent walking around and finding girls.

It was my most important goal so I'd spend 3 hours on it. Daily.

Okay that really helps give me perspective on how much time I could put in. I barely spend 10-20 mins per day approaching before I have to head home. But that's because I had my job and limited time.
Now my job is on summer on break, so I can def do some more!

5/8/25​

​

Approaching today, was a breeze, BUT I didn't hit on any girls. I skated by and fist-bumped a bunch of guys and girls and some of them missed lol.

It has never occurred to me do that while skating!

Campus was SUUUPER sparse, basically students have finished classes and were headed home.

I went to the library. Saw a cute girl working there, asked her about the library hours. Went up the elevator. Came back down, noticed a bunch of fancy people in suits. Said to her, so many fancy people here today. Some kind of event?
"I think its a tour" she said smiling.
Oh cool, have a good one!
You too.

Then I left the library. I took note of how much more relaxed and centered I felt in talking to a girl, period.
I skated around for a bit more before fist bumping one more girl. I said "finished with classes?"
she said "yeah"

dope! fist bump

How bout you? She asked.
I said laughing, uhhh yeah, yup haha.
Have a good one!
"you too" she said.

I skated off.
I fist bumped one more dude before heading home and that was it.

Today I really took a break from all my discipline actions, like doing push-ups and eating under my calorie limit, so I could just do what I felt like doing. I pigged out at work. Truly overate haha. Sent off my comic layouts and now I think I'll go check out the night scene in my town to see how I'll approach it alone.

Some days I wish this phase of life was behind me so I could go back to playing Sonic the Hedgehog games and diving deep into my favorite anime, haha.