There is no algorithmic solution. There is no clear line. It's highly relative.
But in general you can make a distinction between being hijacked by fear vs being wisely cautious. There is a difference between dysfunctional paranoia vs wise caution. If you look both ways before crossing a busy highway, that's not fear, that's wise caution. If you are so terrified of traffic that you refuse to leave your house, that's dysfunctional paranoia. And if you decide to cross the highway without looking because you think traffic is an illusion, you're an idiot.

@trenton It is not helping your situation when you frame it as "stealing from your family".
You are trying to get on your feet. As you do so you can then repay them in other ways. That's what family is about.
Focus on working to strengthen your career into something successful and enjoyable. As you do that, you will naturally become financially independent and you will even have enough left over to help your family out.
Your family will benefit from you having a stable, successful, and enjoyable career. Your career cannot be stable and successful unless it is enjoyable. So don't treat enjoyment as a luxury here. You need to move into a job that you enjoy.

Face difficult situations head on, expose yourself to challenges and massive experience. Live on purpose and make your purpose significant.

I never said he was awesome per se.
Girls get attracted to narcissistic and sociopathic men who know how to push their emotional buttons and have balls.
As a human being, John is bottom of the barrel. But from the perspective of attracting girls, this is a positive.
I'm not telling you to be like John. I'm telling you to be a good person but adopt some the excitement and charm of a scumbag narcissist.
Bottom line: stop being boring. Girls hate boring. Girls would rather sleep with a murder than a boring dude.

5 fucking hours for a date??
This is where you fucked up.
Date should be 2 hrs max and then you lead her to your place or her place.
Of course she will get tired after 5 hrs. You are lucky she stuck out that long.
Your physical escalation wasn't good either.
You didn't lead enough, and you took your eye off the ball. The point is not to spend 5 hrs wining and dining a girl. The point is leading her to sex. You should start doing this from the very start of the date and test her openness to it.

Of course it's their doing. Women can't help but be attracted to the strongest men. The strongest men tend to be extremely selfish and have little empathy.
It's like buying the most vicious attack dog to defend your family and then acting surprised when it bites you in the ass.

"You're kinda hot/cute. Let's grab a drink. I know a good place. What days are you free this week? How about Tues at 8pm?"
Don't just suggest a vague "sometime". You need to grill her in-person on her schedule and set a concrete day and time that works for her. This will triple your results.
Don't call it a "date".

The function of game is to scramble the logical mind.
There will not be sex when the logical mind is active.

You did good.
Yes, keeping a convo going, and keeping it emotional vs logical is the core of game skills. It's not easy to learn that. Takes massive practice.
Also, when you approach a walking girl, you have to approach very assertively, forcing her to stop and commanding her attention. No meek, half-assed, gay approaches. Stop her like you are the police. And be clear about your intent.

Your inner game is lacking. Developing a rock solid inner game is the key. Psychedelics, meditation, awakening is very helpful for this. Your happiness and mood has to be decoupled from external events and people. That means when you're out you're happy doing whatever you're doing just because you appreciate the beauty of consciousness.
Your happiness cannot be coupled to any kind of external result or needing to get something from someone, and certainly not to any reaction from girls. It shouldn't matter to you what girls do or say. Learn to love the present moment more than any girl.

Start with what you already know.
What kind of computer games do you play and enjoy the most? What is it about them that appeals to you? You might get a hint at your life purpose there without necessarily having to look further.
Do you like games focused around money management, trading, economy? Then maybe you'd like business.
Do you like open-world games where you can explore? Then adventure is probably a strong value for you
Do you like creative games like Minecraft where you can build and create things? Then an artistic calling might be suited for you
Puzzle/strategy, sport, simulation, fighting, shooter... they all fill a need and give a good hint at what it is that your soul really craves in life.

Sometimes girls get offended or turned off for random reasons. You can't predict such things.
I told a girl I that she is so young that I am adopting her as my daughter, with benefits. She was into it. Of course another girl might have gotten offended by that. And the key is that I wouldn't give a fuck because I would just go talk to the next 10 girls.
The bottom line is, if a girl is into you, she will let you get away with almost anything verbally. And if she's not into you, she can get pissy about the silliest things you say. So it's not really about you as much as it is about her.
Of course it also matters how you deliver the joke. If you do it from a shitty state it will usually flop and creep girls out. If you do it from solid state and you're fully congruent with it, even the most obnoxious verbals can work, such as, "I'm going to put a baby in your tummy."
In general you should avoid sexually explicit jokes. That is walking the razor's edge and you don't need to do that as a newbie.
Also keep in mind that when you show sexual intent, girls will blow you out more. This is not a bad thing. You're screening out girls who are not DTF. Being platonic will get you way less blowouts but also no sex.
If she can't take a joke, don't apologize, reframe it as her not having a sense of humor. Not all girls will appreciate your style of humor. That's okay. You're just screening those girls out by scaring them off.
A great reframe is something like, "Hey, stop being weird. Don't embarrass me in front of God."
Or the classic: "Hey, don't be racist. You just hate me cause I'm black."

This is a key point.
Social circle requires very good calibration and social skills.

To me career and LP is more important. Dating is like the dessert for getting your life together. But don't wait too long. You can still socialize a bit on the weekends just so that you're not stuck at zero on that front for years.

Bootcamps are mostly for people who struggle just doing an approach at all. The bootcamp simply forces you to approach a lot. It doesn't offer much value beyond that.
There is no magic advice or lesson which you can be told which will make you good at approaching. The only way to get good is to do it a lot and fail a lot.

@bloomer It's how you use your eyes.
Learn to use them properly.
You guys need a few years of eye contact practice.
One of my best wings has been gaming like a beast for 10 years. You know what the #1 thing he still works on when he goes out today?
Eye contact.
Rock solid fundamentals are what get you laid.

I never said you had to date multiple girls at once. One iw fine. But realize that you will get attached and needy with her and this will cost you hot girls.
The hottest girls are attracted to the most detached guys. And realistically the only way you can become that detached is by sleeping with so many hot girls that none of them matter to you.
It's really hard to just attract one hot girl and call it a day and keep her. Realistically the only way you will be able to keep her is if you've slept with even hotter girls in the past, and plenty of them, to the point where you are not clingy with her and her hotness doesn't make you go crazy.
Even if you get super lucky and land a model, you will quickly lose her because you don't have enough masculine groundedness to be the solid man she needs you to be for her.
If only it were so easy.

Look, the reality is that there is a sexual marketplace. Every actor in this marketplace is trying to maximize value. This being the case, of course the highest value actors will tend to hook up with other high value actors.
If you got no game and low social value, then yeah, your looks matter more because you got little else of value to offer.
For looks not to matter so much you gotta develop either game or social value. Ideally both.
The real question here is: How much value are you bringing to the negotiating table as a man? This value can take many different forms, from status to friends to leadership skills to spiritual connection to looks.
When people hook up through dating apps they are basically sorting themselves by looks.

You really can't if you find the girl amazing.
Or, you could if you are seeing a bunch of other girls at once. But this isn't necessarily a good thing.
It's natural to fall for a girl you really like. Of course you will get somewhat needy. That's okay as long as she reciprocates. The key is to make her also fall for you.
Sometimes you're just not going to know why a girl did what she did. There could be many hidden factors at play which you will never know.
It sounds like the thing you could have done better was to indicate your romantic intentions towards her earlier on and escalated in a smoother way. This seems to have taken her by surprise. You want to practice man-woman communication so that it's obvious to her that if she ends up alone with you, sex will naturally happen. There shouldn't be doubts in her mind about your romantic intentions towards her.
And then you gotta learn smooth physical escalation. Going straight to a make out is not the way. You have to gradually seduce her with physical touch.
But anyways, it is rather odd that she wanted to leave. Most girls would not do that at such a late stage.
I mean, you could just ask her why she got cold-feet.

Actually you can see hot girls with average looking guys fairly commonly. Which shows you that looks aren't as important as you think.
When you see short guys, fat guys, bald guys, skinny guys, asian guys, black guys, etc pulling a lot, you will realize it's not the looks so much.
Get some wings who aren't so great looking but pull consistently. This will blow your limiting beliefs apart.

The bottom line is, you need to gain enough mastery over your emotional state such that you feel good and solid most nights out.
Gaming from a depressed state is not really gonna work. Fix your depression. Controlling your state is like the biggest aspect of inner game. Everything else hinges on it. You need to become a generally happy, go-lucky guy who doesn't easily get ungrounded.
Work on enjoying and loving going out and socializing with new people. This is the gold.

Be careful. High likelihood you will come off creepy saying that unless it's really authentic and spontaneous.
The point is that you want to develop the ability to improvise lines like that on-the-fly. Not pre-meditated.
The frame is this: I feel like shit, but I'm still gonna blatantly hit on you. If you do it from that frame it will be funny.
This one is not for newbies. You still need to have a core confidence to pull that off.
Remember, 90% of your game should be friendly-chill, not weird gamey lines.
But it's a great skill to learn to be funny even when you feel like shit.
"Don't come too close to me. God hates me."

"You will be my shoulder to cry on tonight. But also I might make out with you. Just sayin..."
"I'm gonna use your panties to wipe the tears from my eyes."

Get creative with it. Sky's the limit. Amuse yourself and blow sets up. It's better than sitting at home crying.
You shouldn't try to fake being broken though. This is not a technique you use when you're feeling normal.

It's always helpful to be surrounded by women if you're trying to attract women.
But also, if a girl is willing to follow you home, it makes no difference who your roommates are. She's already agreed you're trustworthy enough to fuck. She wouldn't come home with you otherwise.
The hard part is convincing her to follow you home. Once you've done that, you don't have much to worry about. Just lead, escalate, and close.
Building trust with her happens BEFORE you pull her home, not at home. She should already trust you once you bring her home. If not, invest more time and effort building rapport before pulling her home.
Many people live with same-sex roommates. It's no big deal.

"Attractive" is a holisitic quality which involves a lot more than just looks. A girl will think a guy is good looking when she is actually attracted by his status, confidence, masculine vibe, charisma, eye contact, humor, etc.
Solid game makes a guy appear attractive.
But of course some lucky guys simply get laid off their looks. It's not a solid strategy though. Guys who get laid the most are working for it. It doesn't land in their lap.