David Herz, Coach

Is he just not that into me if he isn't pursuing me strongly after 5 dates or is it normal to wait hours/days for him text and ask me out each time?

Maybe I'm old school, but I don't get why a person who is into you would make texting his choice method of communication. I like to actually talk to my partner.

Maybe you should pick up the phone, arrange a date, and actually talk to him and ask him why it takes “so long” for him to text you/ask you out.

Maybe he's just dealing with his everyday life. On the other hand, he might have three other girlfriends. Maybe for him, this is the strongest he's ever pursued someone and he's scared he might smother you. Maybe he's working by some other set of rules.

If you want a relationship, you'll have to learn to communicate. Maybe this is a good place to start practicing that.

Is it a bad sign if a guy doesn't text in the day, takes 1-2 hrs to text back and when he does text, it's after 9 pm to ask me out for a future date?

I think it's a good sign. It might mean he actually has a job that is important to him, or studies, or some other semblance of a life, and that he only bothers with text messages at set times of his day, actually leaving him to be present to the people in front of him when he is with them, including you, when he goes on a date with you instead of trying to have a relationship by text.

Another question from Quora

I've managed to hide it from my family for at least 5 years and now he caught me singing when he made a surprise visit to the house. I'm so embarrased I can't even look at him anymore, I didn't tell my parents I sung cause they would keep making fun of me for doing it and now I'm screwed.

You let him say whatever the heck he wants, you get out there, and get a voice coach, go to every karaoke bar you can, and sing your heart out. You'll get there's nothing wrong with letting out the song that's inside you, and if your parents think that's weird, that's their own damned problem.

Photo by: Ihor Malytskyi

This is an excerpt from my guide, Manning Up: The Guide to Get You Back in the Relationship Game.

First, you will not forget your ex, but until you complete your relationship with her, it is likely to haunt you. (I wrote this originally for guys; if you're not a guy, just switch the pronouns: it should work just as well.)

So here's what I suggest:

1. Thank Her: Sit down and write a letter to her thanking her for every little thing she did with and for you. Acknowledge her for how she made you feel, and for who she was for you.
2. Forgive Her: Make a list for yourself of every way you think you have been slighted by her. Consider that any and all of these things might have come from a place that had nothing to do with you. Maybe she slept with someone else because of her own insecurity, not something that had anything to do with you. Write down at least one reason for each of those things that would make it not about you.
3. Forgive Yourself: You are human. You make mistakes. You screw things up. You might have just killed the best thing you ever had, and just now come to realize it. But as long as you hang on to this, you will not have any chance to see the next great thing, the one that could be ten times better than the best you've ever had. As long as you entertain any conversation that you are a screw up, you will not give yourself permission to be fully in the next relationship. That's a shame, because you deserve a great relationship. So write down every way you were a dick (excuse my language), maybe note where that came from, forgive yourself, and make a commitment not to do that again.
4. Acknowledge Yourself Give yourself credit for everything you were and brought to the relationship. You are great. Notice all the things you did to build the relationship you had. And thank yourself for that. And note that even if your ex didn't get it or appreciate it, you made a difference. And get that that passion was not wasted. Maybe misdirected, but not wasted. Don't let that go. It's part of what makes you the amazing person you are.
5. Learn from Her: Take on that maybe you did have something to do with every thing that happened. I know this sounds the opposite of a previous point; it's not. It's not that anything was wrong or your fault; it's that if you take on that you are cause in the matter, you actually can choose to come from somewhere else. Maybe try “She slept with someone else because she wasn't feeling loved by me. Where could I bring love into the next relationship so that doesn't happen again?”
6. Get that the Next one is NOT YOUR EX: We are human. We look for patterns. We get burned. We say “Aha, I'm not going to let that happen again.” The problem is we start looking for “that.” When we look, we find it. This will kill your love life. I'm not saying be stupid. But don't be suspicious for no reason. That would just be letting some past bad experience haunt you now. Don't let it.
7. Get that the next one is Different: Even if she's your ex's identical twin, she reacts and thinks and loves and hurts diffently. You can not expect to know anything about her because you know anything about humanity, or women, or even her school or family. Let her suprise you.

As a bonus opportunity, you could actually call your ex and ask her if there is any advice she has for you. Thank her for all the stuff in number 1 above. Ask forgiveness, especially if you think it was all her fault. Ask her please to share with you everything that plugged her in or turned her off. There's probably a ton of stuff you just didn't notice.

Only do this if you can avoid reacting or getting angry. You want to learn here so you can be better in the future. Then finally ask her, “What's the one piece of advice, that if I got it, you think would make the biggest difference for me in my next relationship?” and listen like your love life depends on it.

Then thank her and move along. This should be enough to get you complete. If it's not, you've probably got other conversations about relationships not distinguished. If that's the case, then write down everything you say, or even hear, about relationships. Then look at each item and ask yourself if it's true. You'll notice that there are a lot of conversations in the background that could be getting in the way. But the neat thing is, the minute you notice them, you can let them be, and not let them have power over you. You can choose to come from some place else instead.

And once you've got that behind you, come follow me on Facebook, where I share a regular word of encouragement, sprinkled with some questions for a better date.

If I'm 40, is it too late for me to develop a portfolio of skills from scratch that can eventually earn me $10k a month?

No, but you'll have to change your mindset. You write like you need to acquire a whole new skill set of some sort so that you can eventually make a decent living.

The truth is you already have the skill set you need. I am sure there is something that comes ridiculously easy to you. I'll take knife sharpening as an example.

Let's say you can put a razor's edge on a dinner knife without leaving any stray marks on the blade. People want that. They live years with dull knives because they don't want to scratch up their good silver. You teach people how to get a sharp blade, without stray marks, then you do affiliate marketing for the system you use, then you sell them awesome knives. Maybe you branch off into a fine cutlery or silverware business.

The point is that you already know how to do things others don't. Figure out which ones excite you and that you'd love to share your knowledge about.

There is one on-line marketer (Russel Brunson) who started by showing people how to make potato guns.

There are people who do fivver 99design arbitrage, and make a good living at it.

It's just a question of being creative with what you already know. I think a great place to start would be at Altucher Confidential - Ideas for a World Out of Balance. He's got some great advice for keeping you at the top of your game and creating the life you want.

I want to get a job instead of going college. How should I convince my family?

Sometimes you can't, but you can ask them to be patient with you. You can ask them to respect your decisions. You can show them how many people have successfully created their own education outside of the formal structures with which we are familiar.

If you are in the United States, you can also make a good case it's not a sound investment.

Probably the best thing to do would be to share with them your plan. What are you “Yes” planning to do. For instance, if you want to learn a new skill, show them the Coursera/​Udemy/​FutureLearn/​Khan Academy learning plan and then how you will add value to businesses such that they will want to hire you.

Take this as your first test of marketing. Demonstrate to them how your years of business experience gained in lieu of college will actually put you ahead of your peers, and then figure out how you will market yourself for the jobs you want.

Last remind them they were young once too. Maybe if you go out in the world, and discover something you really do want to study, you'll do that much better and be able to go so much deeper because you actually have some experience to draw on.

Parents just want what's best for you. If you can show them that you've really thought it through, and you believe this is it, they should give you some space about it.