IAmA - Professional dating coach. Happy to spend my evening helping the men and women of Reddit find love, sex, etc. AMA!!

How can I boost my selfconfidence? I have terrible problems with my mind. I think I am decent looking, kind of smart and funny and should be a good deal in general, but when it comes to talking to women, there is always this little voice in my head, thinking something like: "Why would she be interested in you? You will just make things awkward!" I know it's bullshit, but I can't help it. Thats why I have such a hard time aproaching woman.

2 problems: 1) you haven't had a lot of success, and success builds confidence. 2) It's because you're outcome oriented man. A lot of dudes have this problem. You get so attached to your fantasy outcome that you're already afraid of losing it. Just enjoy being in the moment, and let go of your attachment to the outcome. Learn to love flirting with women!

Also, I bet the guys who stormed Normandy Beach were scared too, but they did it anyway. Good luck brother!

Wow, thanks for the advice!

I aim to please!

How do i bring up the fact that I like underarms?

Do it during post-sex cuddling after you've been dating for a while. Best to break out the off-beat stuff when you're feeling the closest.

Thank you for a serious answer and not mocking me.

I'm sex positive. We all like weird stuff, who cares as long as nobody is getting hurt.

I am a confident, friendly girl who can talk about anything to anyone for hours - unless it's a guy that I find attractive. I lose the plot and come off looking like a total airhead or weirdo. I have been single for 5 years, I have been on a few dates (some 2nd or 3rd) dates too but they always seem to fizzle out and the guy will say he's not looking for anything serious or long term (although I don't even mention it) I feel like I come across as desperate, even though I'm not. I've tried online dating with no success and I have given up on dating all together. How do I meet someone right for me? And how do I not screw it up?

I need a lot more info. How are you meeting these guys? At what point do you get nervous? What is your age? What are the dates like? Guys are very visual, would you mind posting or sending a picture?

I have met one at a concert, another through friends, and a couple of online dates. I'm 26 years old and I'm not comfortable sending a photo but I am slim with long brown hair, have been told I am pretty. No problem finding a guy who wants to sleep with me, it's finding one who wants to get to know me that's the problem. I'm usually nervous right before the date and sometimes during, I feel like I have to be "on" and can't relax and I end up asking too many questions and it ends up like a job interview. I don't like playing games but I wait a few days, generally wait until they text first, don't double text etc... But it just always fizzles out somehow. I hate talking on the phone or I would call. Generally if they realize I'm not up for sleeping together immediately they say they were just looking for fun, I appreciate the honesty definitely but I can't really continue after that. I cant seem to get past a few days to the point where you really get to know eachother and hang out and enjoy eachother. I know I'm being too general, I apologise!

What part of the country are you in? There are a few places where the women outnumber the men so drastically that it results in a race to the bottom.

I'm in Melbourne, Australia. Big city!

I just read an article yesterday about much of Australia having a man drought... The ratio is a legit issue. It has a major impact on people's mating behavior.

Do you think it's a numbers game? Like, I just don't go in enough dates? I feel like people I know in relationships just fell into them somehow with little to no effort, they just met someone and it instantly snowballed into something deeper. I feel like I'm never going to experience that connection with someone.

It is absolutely a numbers game. Dating is a competitive system.

When I was out playing the field, I'd routinely get 10 phone numbers, get 7 responses to my texts, 3 dates, and 1.5 intimate encounters.

What's your favorite success story?

A student of mine was an awesome guy. Made a lot of money, drove a sports car, fit, handsome, funny, just all around rad. His whole life he'd had no success with women. He was dating a very, very physically and mentally unattractive and mean woman. She dumped HIM in a very mean way.

He worked with me and my former partner, got his confidence up, had a lot of dating and sexual success, and then got married to a total knockout that treats him like gold.

He was my first former student to get married.

I'm a 28 year old virgin. Never even been on a date. Are these things I should be concerned about moving forward? If I ever do go on a date should I be honest about it or should I just act like I've been there before?

This is the only time I ever, ever, ever encourage anyone to be less than truthful. Don't admit you're a virgin. Don't admit it to the women you date, don't admit it to yourself. From this day forward, you are an extremely charming man who has a lot of sexual history. Don't fake it until you make it, fake it until you become it.

I want you to, right now, stop what you're doing. Give yourself permission to have sex. Clean your apartment. Get your bedroom ready for sex. Go to the grocery store and buy a box of condoms (even if you already have some).

I want you to affirm to yourself on a regular basis that sex isn't a big deal. It's something that just happens as part of the regular course of two consenting adult's lives.

It is also time to cut porn out of your life. Switch to POV porn when you NEED it, and try to visualize it being real.

Your next step is to attempt to sleep with any woman that will have you, even a prostitute if that's legal in your area. It might not be special, but it is time to pull off the band aid.

My God, are you sure???

Yes

I sent you PM with my question, interesting AMA, btw!

Thanks a lot, I responded.

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Who dude, I'd definitely say that the common theme in those relationships is you. Problems that major are a little over my pay grade I'm afraid. Might be a good time to see a relationship counselor.

Also, you might end up bitter. If you're going to be bitter, might as well head over to /r/theredpill. A lot of what they say isn't wrong, it's just the most pessimistic version possible.

Do you think that should be the prevailing attitude that men should take? A seemingly dystopic, almost cynancle approach?

What are your thoughts on feminism?

Do you think with how you have developed as a seducer, would you say that you have a high probability of being with a faithful woman your whole life?

How about PUA philosophy? I knew a dating coach a while ago who hates the PUA approach.

No. Not too much. Too cynical is definitely not the right place to be. When it comes to all the redpill stuff... Women can be very cruel to men they don't respect, but those that would be cruel still treat men they respect very, very well.

I'm very in favor of gender equality, equal rights for men, women, glbt folks, all that. I'm not a fan of the feminist movement as it stands. I feel like the movement itself has lost the plot. Too focused on a few buzz words and a victim mentality. Not focused enough on having high standards for what women can achieve. I spend a lot of time on /r/feminism and you never see them talk about helping women become the most competent. I'm more inclined to think that we should do things like abolish softball because women are perfectly capable of playing baseball with the boys if they set their mind to it.

I would say that I have a lower risk of being cheated on. I know the warning signs better than most guys probably do, I'm way way choosier about who I'll get into a committed relationship with. Most importantly, I'm better at keeping my partner happy.

PUA can be cool depending on who teaches it. I always thought Mystery Method was a lot of fine, and I like RSD's theories on doing a ton of approaches. I think PUA gives shy guys a great opportunity to see that women can respond well to them in social situations. I don't think it's the end all be all of personal growth.

Also. A brief summary of the warning signs she'll exhibit?

Sure...

She'll be more apt to get angry about little non-issues. She'll be less likely to perform fellatio. Less likely to have an orgasm during sex. You'll find her telling weird little lies about who/what/why/where she was. Changes in her behavior. Changes in how she looks at you...

This is a great response. Sucks your ama didn't take off like the others. Thanks!

Sometimes you win sometimes you don't/

What's the best tip you can give to men for online dating? What's the best thing to do/place to go for a first date?

Online dating is pretty toxic unless you're outstanding at the 3 H's: How tall are you? How cool is your job? How good do you look in pictures?

The top 5-10% of men, as judged on those 3 categories, basically sleep with whatever women they want. The bottom 50% don't even get replies.

Best first date is simply taking her along to do the cool stuff you were already going to do that day. That's also the best second date. And the best 100th date.

Holy fuck man. This website. It's like dating insight from Jesus. I read the 14 points, of which I'm missing some. Yeah, some. Dick. But seriously, great stuff. Thanks for putting me on to it.

Awesome man, I appreciate that!!!

Have you seen Hitch?

Yeah, good movie. I wish this line of work would actually pay for a lifestyle like that. lol

I have a few questions for you.

1) I have watched, "The Millionaire Matchmaker" before with Patti Stanger. I know it's a reality show but I can't help but wonder if there is any truth to this show and it's not staged. Have you ever watched this show and do you find her to be a legit matchmaker like she claims to be?

2) How did you get into this profession? What did you go to school for?

3) Is this profession considered a private one, as in you work independently? How nice is your salary?

4) I find it very easy to dish out advice to others mainly in regards to relationships, but when it comes to my own relationship I can't eat my own words. Is that typical? (Assuming you maybe able to answer this)

1) I've caught it here or there, but I try really hard to avoid passive entertainment. I think most of those matchmaker deals are put-on though. I messed around with a couple of the big chains that do that, and I wasn't impressed. $3500 for 15 dates in a year? The guys I teach usually end up paying way less than that for way better results.

2) I studied anthropology in school. There's no real certification process, it was really more a matter of studying the subject to the point of ridiculousness, building a framework and techniques, testing them, refining them, giving them out for free, and then turning it into a marketable product.

3) Yeah, I'm an independent coach. There are jobs out there working for bigger companies. I've pulled in some pretty good dough here or there, but I'm not as interested in the hands on coaching these days. The marketing aspect makes me sick to my stomach... too much of a rent-a-friend vibe, and I don't like that.

4) Yes, totally typical. When it's your own life, it can be very hard to see the forest from the trees.

What's the biggest mistake a man can make on a first date?

By taking her on a boring job-interview style date.

You should be taking her along to do the cool stuff you'd be doing anyway.

Also, poor eye contact. Look her in the eyes almost all the time, but remember to blink if you're nervous. Making sure you smell good is always important, and so is all of the normal hygene stuff really.

Hey! thanks for doing this ama! Just a couple questions I have already pondered before, but would love to hear your stories!

Have you ever had to give up on a client before?

What percentage of your clients do you think have had successful lasting relationships from your coaching?

What Is your relationship status?

I've definitely given up on a potential client, but not one I've accepted for coaching. It was because he had real issues that needed to be addressed before he could work on his dating life. Like major mental issues.

All of my clients have been successful. They all start with a goal, and they have all met the goal. I'll keep working for free if they fall a bit short because I'm passionate about helping them.

I'm in an awesome relationship with a super hot redhead. We've been together for about 3 years with a little hiccup at the beginning before we were exclusive (I was kind of a jerk, insisting we keep the relationship open. She was willing to do it but it didn't make her happy so I broke up with her. Got back together when I realized that she was absolutely awesome to me even when I didn't return the favor. I learned my lesson.)

How do you deal with haters?

I send em this video: http://www.youtube.com/watch?v=_PoroSoXfME

I have to compliment you - you are extremely thorough and thoughtful in you answers. And I generally agree with the advice you are giving people.

My question is, what do you think about the whole PUA community and their way of doing things?

Thanks man, I try really hard.

I actually like PUA stuff to a certain extent. I dabbled in that scene for a bit, and presented at some lair events. I think it's a cool opportunity for previously shy men to see women respond well to them. I don't think it's where people should stop when they're trying to self improve.

What do you think about - "It is better to prevent than to cure", that is said by all the medics? Do you think that following this rule in relationships can prevent from STD and broken heart?

Are you suggesting sometimes to follow only rationality, or only instincts?

Or do you think humans must also learn from their mistakes and defend themselves by acquired reflexes, after any wrong partner that made them smarter, if still alive?

Yes, absolutely.

No, use rationality as a check and balance to instinct.

There's no bad way to learn.

These are really deep questions man. Like really deep.

What's the best way to end a date if I'm not interested in the person after meeting them? I was recently in this situation and I wanted nothing more than to cut it short but it felt rude to me.

Be honest, direct, and get the F out of there fast in case they're crazy.

So is it literally just something like "hey I'm not feeling the vibe, deuces"?

Yes, exactly.

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One of the benefits of being a guy is that looks don't have the impact on your dating success that they do for women. Plenty of men who are very physically unattractive are extremely successful with women; Donald Trump for example.

You've got a lot of control over your looks too; fitness, grooming, posture, style... All of that counts for more than genetic good looks.

As far as the second part of your question, you're asking for a few tips that will work as a cure-all, but unfortunately it's not quite that easy. I will say a good starting point though; Always have great posture, and always try to be the most social person in the room!!!

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It can be done. Sean Stephenson, the motivational speaker, is probably in worse shape than you and he has a very lovely wife: http://www.youtube.com/watch?v=W32o2OaueeE

What is the average problem that people come to you with?(like, "I'm having trouble asking women/men out", or "I don't do well on first dates" etc.)

There are so many... Most of them are something like:

Guy - "Hey, I've never had a lot of success with women, and I feel like I should have. I'm getting older and I want to have a family some day. What do I do?"

Girls either - a) Guys don't talk to me. b) Guys will sleep with me but won't commit.

I have just one more question, do you find women have a problem with tatoos?

No, quite the opposite. Unless they're shitty tattoos.

good, i got one just last week, and i've been freaking out that potential dates might find it off putting

What is it?

I am in a relationship already, what are some general tips to keeping my relationship fun and exciting?

"I am in a relationship already, what are some general tips to keeping my relationship fun and exciting?"

Are you a man or a woman?

I am a man (Dating a woman)

Fantastic.

1) Lead the dance. Don't be a tyrant, but have a strong vision of the lifestyle you want to have with her, show it to her and lead her to it.

2) All women will test your boundaries. Men with no boundaries eventually end up getting walked on. If you like watching golf on Sunday, do it. Your boundaries are very attractive, and sticking to them make women feel safe.

3) Don't get into sexual routines.

I'm a recent widower in my early forties. No children, but I do want them someday. It will be a little while before I'm able to date again. What are the chances that I will meet and attract someone young enough to have children with? And how can I ensure that I will be emotionally available when I do?

100%. If I remember right, 15% of women have a straight up fetish for older men, and a much higher % is open to the idea.

The difference is, when you're young your physicality tells them you're on the dating market. When you're older, you have to do the work. Fitness, manner of dress, grooming, style, keeping away things like ear hair and bushy eyebrows... Once you've got all that down, the other challenge is access. Younger women (18-29) will think it's creepy if you try and meet them through the traditional channels like bars. It takes some creativity to find those opportunities.

What do you think about the theory that a perfect partner must be like a brother / sister - similar physically and mentally? By this I mean looking alike physically the most possible, having the same tastes and hobbies, and being from the same social environment?

Or you belive that anybody can stay with somebody even if they are complete opposite of each other?

I don't think commonalities are that important.

I like the David Dieda concept of masculine and feminine polarity. I think it's important for men to have their mate be and activity partner. I think it's important for the woman in the relationship to have a huge amount of respect for the man.

How this concept relates to masculism, machismo and sexism?

IMHO, he doesn't mean the woman needs to defer and respect the man simply because he's male, but rather, he needs to truly earn her respect by generally being a good man

Yup!

I feel like traditional gender roles are preferred by most people. I target my advice to the widest part of the bell curve.

People who don't prefer traditional gender roles need to have their rights and preferences protected and respected. Its just not usually useful to give generalized dating advice to outliers because you might be an outlier in one area and average in another.

Hope I'm not too late.

I am a student that does not have a car. I'm not a broke bum, I'm just a shitty driver and I much prefer to walk to school and to my job. This tends to be a turnoff for women because usually not having a car is a dealbreaker. I don't want to spend money on a car and insurance when I'm pretty happy without one. Tips on overcoming this obstacle?

Absolutely. Stop talking about it like it is something that's wrong with you, and start owning it as a life decision.

"Hey, let's meet here at this time." "I don't drive." in kind of a stern and rebellious tone. "What?" "I don't drive. I don't want the hassle. I like to be off the books."

It's amazing what you can do with semantics. "I can't afford it" sounds so much worse than "I don't wanna spend the money."

Exactly. It's not semantics though, it's a little window into your frame of mind. The original commenter has clearly made a bold life decision, and he should own it like a bold life decision. It's not something that he's subjected to that's out of his control. He's being a strong leader and a strong man about it. Now he just has to sell it that way.

How to do you get a girl to text often? I am interested in a girl who live over an hour from where I live and I asked for her number. We did texted a bit but apparently she stopped replying. I asked one of her best friends and said she rarely text at all. So any ideas?

Edit: high school dating btw

Instead of writing a blurb here, check out this awesome article I wrote on text game:

http://iwillteachyoutogetlaid.com/?p=45

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Lots and lots of painstaking research.

How did you get into the field? Would you say what you do is unique to you or do you follow a prescribed methodology? If so what? Do you feel like the skills you have developed have had an impact on the way you would market your blogs?

I studied anth, did a lot of reading, built a methodology and an intellectual framework for how dating works, tested it, refined it, tested it, refined it, taught it, then started teaching it for money.

I'd say what I do is pretty unique. I try to pull good ideas from anywhere I can find them. From Dear Abby and Cosmo all the way to Mystery and PUA stuff, and back again. I'm a huge nerd for social anth and human mating behavior.

I think they have a bigger impact on the women's blog. Most dating advice for women is pretty bad, but it's very palatable. They write what sells. I try to be committed to telling the truth and being blunt. Too much dating advice for women is kind of like soft bigotry, like they have a low opinion of their reader's ability to be introspective.

Been with a girl four years on and off and one off those off periods was fir a few months with another girl who I have since broke contact with now current gf will soon be moving in and I stl worry that she hasn't gotten over the hurt and mistrust and regained the level of self esteem she had a year ago before I practically "left her for another woman"

The best thing you can do is to consistently do right by her. Do the right thing consistently and for long enough, and she'll eventually learn to trust you more. If you're moving in together, it sounds like it is going well.

I'm not a relationship counselor though, just a dating coach, so take as an opinion and not a diagnosis.

Yeah I'm actually probably quasi sex crazed wouldn't say addicted and have major depressive disorder so the flirting and pick up game have always been A. A way to fulfill the desire for meaningless sex and B. A confidence booster for myself so I guess follow up question what would you suggest to help me feel less need for that...it has diminished but it's not yet completely gone

That's drifting into counseling territory again, but I would say that external validation isn't as good as internal validation. Focus on what you like about you.

Figured I'd hit the deeper questions before this thing exploded thanks for your time and advice and if things don't improve we may seek counseling but I hire it won't come to needing that

Absolutely man, hope that helped!

What is your opinions on taking a break in a relationship? I've been with my boyfriend for 6 years and recently have been considering taking a break from the relationship and moving out. I've lived with him since 6 months in to the relationship and never felt like we had that time to miss each other.

It is very very hard to move a relationship backwards.

Also, if you're taking a break, you're probably taking a break so you can see other people. Are you going to want to take your boyfriend back after he sleeps with two or three other women?

I don't think I would like if he saw other people, but I feel like I'm smothered. I don't think that I'm happy with him anymore, but the very thought for not having him around anymore gives me an anxiety attack since I don't have anyone here for me (friends, family,etc). I'm not sure where to go from here.

Why don't you focus on finding a better sense of self while in the relationship? Make new friends, get new hobbies, improve your professional life, and then if you still aren't feeling things you'll be more comfortable in breaking it off.

The only problem is that he might sense you pulling away and get even more clingy, which will drive you further away... Sounds like you'd be over things if you had a better social network anyway.

What all goes in to being a dating coach? What can you teach your students, and what things do they have to learn on their own?

Depends on the students. A lot of dating coaches have a complete methodology that they try and get you to implement. I try really hard to just not fix what isn't broken.

The main thing a student needs is the willingness to learn. The willingness to look themselves in the mirror, take responsibility for their lifestyle, and decide that they've been doing it wrong.

What advice would you give to someone a bit shorter than average? I'm not the shortest guy out there, but certainly not the tallest (I'm 5'6".) It just always seems like my taller friends get more success with women.

I have a buddy that does pretty well and is your height.

The best thing you... You might be 5'6" but your personality can be 7' tall. You should try to be loud, confident, and outgoing. But especially loud.

It also helps if there's something outstanding about you. Singing, standup comedy, something like that.

What if you're not naturally loud? Fake it 'till you make it?

Yes

So are you like hitch then? From the movie hitch..

I was, now I mostly focus on media and stuff.

Have you ever felt like youve scammed money off of people?

Never. I'd rather work for free than take a dollar I didn't deserve.

What to do if if she is unsure if she likes you or not? Her friends says she does, but she seems to hide it well.

Is she unsure or are you unsure?

If you think she likes you, just go for it man no hesitation. If you're wrong, date her friends.

How do I know if a guy is serious or playing around?

Does he invest in you? His time, his gas, his money, his effort?

Also,

Does he cuddle with you in bed after sex, or is he up and gone ASAP?

You are good man Mr. Masterson, good luck with your Redhead!

It's not luck, it's skill ;)

Right now my life consists of school, work, and home. I usually don't really go out unless its with a couple friends. Where can I go/what can I start doing to meet more women?

Take dance lessons.

So, I'm a 29yr old single mother (7yr old boy, good relationship with his father, no nasty baggage there), short, chubbyish (but sporty, love my running and gym), I have a good career (nurse), love life, positive personality, happy, confident, but can't find any men, I don't know where to look (online was no good, no one seemed interested in chatting, I would send messages and no one would reply!) and I'm new to the city so no chance of meeting men via friends/social gatherings as I'm still working on the friend finding! I feel like all the men my age are married or gay (or total meat head players) or very different because I was a raising a baby while they were traveling overseas and partying it up, I also think my independence puts men off.

So any suggestions? (I am actually quite happy being single, so theres no air of desperation around me putting men off either)

Male attraction can be broken down into two stages: Physical attraction, and then emotional attraction. Physical attraction gets them to come around, emotional attraction gets them to stick around.

If men aren't coming around, it might be a physical attraction issue. If you're comfortable, send a picture and I'll see if there's anything about your vibe that we can tweak.

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Liking her just less than she likes you.

Good eye contact, and thinking sexual thoughts when you look her in the eye.

Touching her on the elbow when you first meet.

There are a million.

Hey Dan, appreciate the Ama. I have heard a good initial communication with women should should be to ask them lots of questions about themselves. Would you see that as an annoying approach or a fine approach?

Annoying for the most parts. If you just met a girl and are trying to get to know her, the best way to keep the conversation going is by asking open-ended-feeling-questions. Don't ask "Where are you from?" ask "What was it like growing up in your home town?"

In a relationship (I've been with him for a year now, still pretty fresh) when do you know when "enough is enough"? I constantly find myself compromising because, well, that's how ya do to make it work sometimes... & I get it's up to me when that level has reached... But I guess I'm asking if there's a point in a healthy relationship when you don't feel your SO is compromising as much as you do for them... And when and if there's a time point when you know it will stay this way or there's still time for it to evolve?

I try to encourage people to really know themselves. What are your deal breakers? Where are you willing to be flexible? Once you know yourself and what you truly need to be happy, then it's time to go get a long term relationship (if that's what you're into).

I have had lackluster success romantically, and have been stuck in a rut for a while. My mind keeps drifting to a past relationship that ended on a pretty negative note. It's hard for me to trust and let go of the past and I find myself missing the person who caused me pain out of loneliness. I'm a mixed bag of good traits (funny, smart) and bad ones (insecure, untrusting) and physically meh. Even today, I was just rejected. What advice do you think would best benefit me, in your experience?

TL;DR I'm meh looking with an alleged good personality. Got trust issues. I'm giving her all she's got Cap'n and I just can't do it. Any advice?

Confidence.

That's kind of a catch-all though and probably not helpful without context. Here man, here's a blog post I wrote about the 14 most important things: http://iwillteachyoutogetlaid.com/?p=75

Work on those. If you have all 14, you'll clean up. If you're missing more than 2, that's your first problem.

Thanks for the reply, and the Ama. Non-Me question: Did you always have success in relationships or did it come later?

No not at all. I did in high school, but when I got to college I fell on my face. I went 2 years without being touched by another person. Then finally I realized that I was running out of college and I had better figure it out. So I did. Then even once I was successful, I realized I was really passionate about the subject so I kept at it. Next thing I knew I was a dating coach.

I was skeptical but this is a great list. Every straight guy should honestly follow these 14 things. I know most girls already do (innately & subconciously).

Thanks man, I worked very very hard on that on a napkin at a bar.

I'm familiar with love and sex, but I'm intrigued by this "etc" of which you speak. Clarify if you could.

Lifestyle, professional, fashion, friendships, etc..

Hi. Would you advice the system of the four basic questions about favourite book, song, film or videogame as the first approach, in order to stay neutral in the realm of equity, and not annoying the interested person?

I was able to meet a lot of people this way, what is your opinion?

I think that approach would work fine on guys.

If you're trying to talk to women, it is usually more interesting for them if you ask questions about feelings. Don't ask "Where are you from?" ask "What was it like growing up in your home town?"

Do you mean women in general, the majority, or there are only groups of women that like this specific approach?

The majority of women. There are always exceptions. Everyone is a little bit different. I try to aim my advice at the wide part of the bell curve.

Have you read Neill Strauss' 'The Game'? What did you think of it and does it align with your theorems?

Yeah I have. I think it's a really good book that is also a big piece of marketing material.

Mystery method / Style /etc... They have some good concepts and I think their stuff is a great magic feather so that shy guys can see women react to them positively. I try to understand why their methods work, and then see how guys can get the same results without having to put on a show and do/say made-up stuff.

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I don't like the word slut. I don't like anything that discourages women from sleeping with me. I don't want to shame or judge women for expressing themselves sexually. Thinking of things in those terms will stop you from getting laid some day.

If you don't like the girl, breaking it off with her shouldn't hurt your friend. Just be respectful, firm, and concise.

Would you ever advice someone - “It is better to be alone than in bad company.” by George Washington? Or it might conflict with your profession?

Absolutely. You should only be with someone that meets your needs.

I know a girl that I really like but never really tried to talk to for over 3 years now. She goes to my school and is really nice. We seem to have a few things in common because I would sometimes overhear her conversations in class. Her parents and my parents get along well and know the deal between the both of us, and they are trying to get us two together. We happen to go to the same parties, because we somehow happen to be friends with the same people. Sadly, just when she started to confide with me a bit, she avoids me because I tend to look at her A LOT and thinks that i'm creepy. I don't talk much, and some of her friends think i'm a bit of a loser. The reason I never asked her out because the people that she hangs out who view me as a weirdo might mock me. I have gained some confidence overtime, so I might make my move next week or so. How should I approach without making myself look stupid and awkward?

Sounds like you're probably in school still. What you need to do is up your fashion and fitness, and try to make friends with her friends...

...Actually, what you REALLY need to do is forget about all this, and just work on your social skills. Try to make friends with everyone. Make sure you know how to groom yourself properly and dress well. Join clubs. Go to parties. Play sports. The girls will find you when you're the most social guy.

What are your thoughts on the book I Heart Female Orgasm?

I haven't read it, but the concept is awesome. Anything that helps people feel more confident and informed about their sexuality is great.

I have a couple super close male friends. Will this intimidate the men I am seeing?

A little bit. They'll more than likely be un-trusting of your male friends at first.

Be honest, do the male friends have a thing for you?

Hey, whenever I'm around any girls it seems like I just blank out on things to say. What are some good conversation starting topics?

That happens for a very specific reason; you're filtering yourself.

Imagine you have $100 of mental energy to spend. Instead of spending all $100 being engaged in the conversation and letting your subconscious think up fun things to say, you're spending $80 second guessing everything you think of.

Shut off brain, open mouth.

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You don't need to tell her, show her;

-Try to see her more than once a week.

-Cuddle with her after sex.

Generally speaking though, your best bet is to let her move to advance the relationship.

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The best way to get out of a second date depends on what your goals are. Getting out of the date is as easy as just saying "I don't think of you like that." but then he might not want to be friends anymore...

How do I not come across as goofy when speaking to women folk?

Stand up straight, good eye contact, be the most relaxed person in the room when it comes to bodylanguage, and use a deeper and slightly louder voice than normal.

I have dated a girl for about three months and I really think I love her, Should I tell her I love her or should I wait?

Wait. Always let her progress the relationship.

I have an unusual one.

I grew up poor but went to schools for the wealthy (a combination of hardworking parents and scholarships.) I'm already working as a young professional but still live with my parents (in my early twenties, which is normal for my Asian country.) Most of my peers are wealthy and make up my available dating circle. I've always been insecure about letting people in because I've grown up knowing the disparity between my economic background and those around me; there's also a feeling of impostor syndrome whenever I make new friends since I was lumped in with the rich kids growing up. This has manifested itself in my dating life in that I don't let people get too close to me for fear of them seeing where I live (and figuring out/resenting me for the "impostor" that I am for speaking and acting like them despite not being "of their class.") I'd like to break this cycle of insecurity. How should I start?

You're way more worried about it than they are. People are like the T-rex in Jurassic park; they can't see your weaknesses until you're self conscious about them. If anything, they'll respect you more for overcoming those limitations. Wear it like a badge of honor, and be proud of it.

Thanks for this AMA and responding to all these questions. What advice do you have for a male in a new city, who doesn't really know anyone or have social networks, to get into the game?

Start being the most social person. Talk to everyone in social situations. Always be the most social person in the room.

New York City has a really messed up gender ratio. There are SOOO many more women than men. The men go west to find work just like they always have, the women tend to stay home.

Because of the crazy ratio, once you start to meet women, don't do too much in the way of courtship. No fancy dates or flowers. Focus on hanging out low key.

Maybe a bit late, but for example you have basically no hobbies and sit behind your PC all day what can I talk about that might interest her? Saying I sit behind my PC and browse reddit MIGHT not be a turn on.

I'm going to be honest with you, that's not a very attractive lifestyle. Ideally you try and fill your life with interesting things, and bring her along to go do the interesting things.

That being said, thanks to Reddit you should be able to talk to her at length about art, music, politics, philosophy, science, and cat pictures.

True but I go to school from 9-18 every day then i come home around 19 then I eat dinner and hit the gym afterwards I browse reddit and go to sleep. Not much I can do more atleast thats what it feels like for me. Atleast I got a bright future as an accountant for a big 4 company?

Yup, sounds like you're trading some of your dating life now for being a little bit of higher social status later. Good plan, but don't wait too long!

Hi it seems that for me when it comes to asking women out I always let my mind become clouded with negativity or uncertainty. This is my current situation. I feel like I have a connection with them but I always seem to psych myself out. What advice can you give me in order to avoid all this negativity and just go for it?

This issue is the result of your mentality. You're thinking of things in terms of trying to get the girl, or get in her pants, or get something in general. Stop thinking of it in those terms, and start thinking of it in terms of whether or not you're a good match, and whether or not she is compatible with the real, genuine you. Also, try to live in the moment. Just enjoy time with her. Don't worry about the outcome. If you become attached to the outcome, and put yourself in the frame of mind where you're afraid of losing something you don't have yet.

Awesome thanks for your advice! One other question though, when it comes to asking them out, would you recommend asking them out like right away when you meet them or giving it time to see if you really are a match?

I don't believe in popular culture's version of the traditional dating framework. Your goal should be to invite them to do the cool stuff you're doing anyway. So if you met someone that you think is cool, and you feel like having them along to do the cool stuff you're going to be doing, invite them along.

Say you meet a girl at a bar, get her number, text a few times. "Hey, I'm going for a motorcycle ride Saturday afternoon. You should come."

That sort of situation is WAY better than the job-interview style date where you sit across a table and judge each other... and if the other person flakes, you still get to spend your time having fun. AND it makes you more attractive because you're the kind of person that does interesting things.