I’ve helped real life versions of the “40 year old virgin” meet and attract women. I’m a professional matchmaker, date and attraction coach, and cheerleader of self-development. AMA

Do you ever turn clients down? Can you give an example of who/why? or several if there are some good stories....

All the time :) Joking! I would say about 20% of the time. Here are some examples:

• A man in his 40's who only dated college women up until he chatted with me. Combine that with him touching my leg during our initial consultation and we had a no-go. I later heard that he demanded a refund from a colleague of mine who worked with him. He was trouble.

• A man his 20's who clearly had Apergers and had not yet been diagnosed or worked with that issue first.

• A female CEO of a tech firm in SF, who was overly demanding and only wanted a Harvard-educated, fellow CEO with stunning good looks. That's not love, that's superficiality.

That's just a small highlight. Hope it answered your question!

The aspergers guy must have been hard to deal with. There is one on reddit who consistently posts AMA about him masturbating on webcam for money, then violently argues with anyone who has an opinion about it and calls everyone trolls. I feel bad but at the same time I dont.

How do you know this guy had aspergers? Whatever he is dealing with, he sounds like a real headache.

The one I referred to wasn't hard to deal with. It was just a disappointment for him. He actually handled the rejection much better than the other two candidates I mentioned.

The reaction of the last one (the female CEO) was the one that disturbed me. I'd rather not share the details but let's just say she believed that money could buy her anyone. Truly. Plus, she made a matchmaker before me cry, and that's never a good sign, is it?

Best advice for someone who hasn't dated in 5 years? Most traggic person you've come across? Anyone you've had to give up on? Most inspiring story!?

1. I would encourage you to create an action plan and stick to it. When people have been outside of the dating game for a while they can become passive. If you're serious about dating then ask yourself what you have to do to get where you want to be. Then create a tangible plan and go for it. Best of luck.

2. No tragedies luckily. Although I guess folks who are looking for a resume (6'2, CEO, Ivy educated, and piercing blue eyes) are tragic in their own way :-) I don't work with folks like that.

3. Most inspiring story: A client in his early 40's with ZERO dating experience being able to date confidently within 3 months. He's turning into quite the charmer. He's such a good guy, so the transformation is one that allows him to show women how awesome he is instead of masking any insecurities or vices.

How do you make a profit?

Excellent question.

I used to matchmake and coach for a company. When I created my own practice, most of my clients continued to work with me. I attract clients through word of month and referrals.

I work with 6 to 12 clients a month, very closely. It's like having a group of friends you are strongly supporting and cheerleading. Most coaches who love their job will tell you the same!

When you work with such a small client base, you have to be charging on the relatively high end. Do you notice a trend in the types of clients that you see?

Here are some examples of types of clients and services requested.

Students or folks on a strict budget = pure coaching services

Male engineers = a combo of matching/coaching

Professional women who want kids asap = pure matchmaking services

You hit the nail on the head that it is on the higher end. Like any coaching/consulting practice it has to be if you want results.

Matchmaking clients are almost always in the higher income bracket with a few exceptions. Think: middle class and up. I suspect it's because when folks can afford it, they want to outsource what can be a very time-intensive search.

Coaching clients are all over the map, however. I suspect it's because folks are willing to invest in something they can use over and over again (in this case, a new dating skillset and mindset).

Thanks for your response. I can see how this would be very rewarding work - good luck.

Thank you! Good luck to you.

what would you tell someone (straight male) whom hasn't dated in awhile? what are some common mistakes i can avoid and that sort of thing?

Great question! First and foremost I would say look at any past experiences you've had with rejection and deal with any trauma or anxiety around that first. You want to become "rejection-proof". The more you can laugh in the face of rejection, the more success and happiness you'll have in your love life. Then educate yourself. Dating is a social skillset - you can learn it, but it takes experimentation, and you have to accept that you will be rejected. Good luck :)

What would be some general tips/advice that you would give to get people active on the dating scene?

What would be the client's hesitation/reluctance to do so in the first place?

Love this question! Thanks Krispy89. Here are 5 Do's and Don'ts

--DO online dating (the horror, I know)

Don't exhaust yourself with serial dating. It will start to become an interview process and that's the best way to get sad quickly.

--DO some serious self examination. Ask yourself these key questions: do you embody the qualities that your ideal partner would appreciate? If not, are you cultivating those qualities?

Don't think you have to be "perfect" before you can attract a great partner

--DO experiment and date different folks, allowing for the fact that attraction can grow

Don't continue dating someone you were never attracted to in the first place. I've had one too many female clients who tried to force themselves to date a guy they had no attraction towards.

--DO Good hygiene

Don't ignore this advice. Seriously. Brush your tongue too.

--DO find love everywhere and recognize it comes in different forms. You'll be less obsessive when you're active on the dating scene. When you recognize your life is full and complete already, you can be present and aware of someone else in a more generous way. You can be more in tune with who that person is instead of focusing on whether they fulfill what you want

Don't give up on romantic love.

I hope that was helpful! xoxo

Some great advice there. I'll be sure to send some Reddit Gold to you, kind stranger :D

EDIT: Gold is on it's way to you. Easier than I thought.

Gold! Feeling special, thank you Krispy89 :)

Two part question:

1.) How do you feel about online dating

2.) Do you think it encourages "resume" dating? And is that ultimately good or bed for people? (eg, I won't date anyone who isn't a brunette, grey eyed, over 5'8, a polka music fan, pescatarian, drives a 2006 model year car or later, etc. etc.)

1) I love online dating. It's all about how you use it.

2a) You're right it can and does encourage resume dating in some.

2b) Not healthy though I love your example. A brunette with grey eyes driving down the road in her 2006 car blasting polka music is a hard find.

What are some good ways to use online dating that people overlook? Or typical mistakes?

Some quick tips :-)

1. Pictures pictures pictures. They're the most important part of your profile.

2. Have someone you trust to give you constructive criticism. I've had a number of clients say "oh yeah, my sister told me that picture/profile paragraph/message was horrible, but I didn't listen". Don't rely fully on your Mom because she has Mom goggles.

3. Talk about what you DO want, not what you don't. e.g "attention, all you girls with daddy issues and gold-diggers: you need not apply" - yikes, now that's a turn off. More subtle statements of "I don't want X or Y" are also a turn off if there's too many of them. My best guess of the psychology behind it: we, as the reader, automatically think you may be a negative person and/or accusing us of those qualities. It's not necessarily fair or rational but it is a turn off regardless.

4. Think of online dating as the sexy cousin of LinkedIn. You're still marketing yourself and you have to focus on impressing your audience, but it's more fun (unless you really love LinkedIn?).

5. Speaking of impressing your audience = no generic messages. This note is especially for men, since they have to do more of the pursuing. Even if you created a special message for someone, if she can't tell you personalized it for her, she's less likely to respond.

What is your top advice happily married couples that have been married for 20 years to stay happy?

Sex life. Prioritize it.

Gratitude. This person is choosing to spend their life with you. Are you making it clear you appreciate them for it?

Self Worth. Are they grateful for you, and what you're offering, and showing it?

Which brings me to communication. All of the above takes open and sometimes difficult communication. And trust me - it's worth it.

On a final note...we live in a culture that is highly conventional when it comes to love. Polyamory is something I think everyone should consider. For those who are not clear on the term, please research what polyamory is (hint: it's not sleeping around without telling your partner). At the end of the day, we all want to be happy, and there is more than one way to ice the proverbial cake.

You were going great until the end.

Seriously if someone is honestly putting the best of themselves into their relationship with their spouse, raising children, and a career how is one supposed to find time to find fuck buddies? What a joke.

I'm pretty sure it wouldn't make you feel better if I said I was 80 and still going strong :-) As I mentioned above, Polyamory is not about sleeping around. I suggest you do a little research before you post again. Then come back to me with a more well thought out question or response.

I'm a single man with a good friend who is a single woman. We're both looking for people to date and often go out together, just the two of us. I'm not interested in dating her and we've been friends for years. I'm pretty social and like to talk to lots of people, she's more of a "let's sit in this booth and have a conversation" type.

Do you have any suggestions how I can be a good wingman and help her meet guys? And vice-versa - how can she be a good wingwoman for me? Also I get that it's easy for other people to assume we're together which might confuse someone who would otherwise be interested in one of us - how can we minimize that while still enjoying ourselves?

Fantastic questions. Wingmaning/wingwomaning is one of the greatest gifts we can give our single friends! And oh boy, can we do the gift-giving in this department in all the wrong ways.

Let me give you an example. Women (a) understand that other women can be a wingwoman for their guy friends, and (b) they like men who are assertive. For some reason, some women forget both those points when they want to help their guy buddy. So Rachel, for example, will spark a conversation with a woman that their friend is interested in by saying, for example: "hey! your earrings are beautiful!" immediately followed by "oh by the way, this is my buddy Michael. Excuse me while I go the ladies room". This is very well intentioned (bonus points) but it's far too obvious (major minus points). Ultimately it hurts Michael because he'll appear as if he isn't assertive and is relying on Rachel to introduce him to women. Quick turn off. The introduction to Miss Cutie is no longer useful.

Contrast that with a more subtle approach. Rachel can strike a conversation with an individual in the same group of friends that Miss Cutie is in. She can take her time and, with a bit of luck, be introduced to other members (like Miss Cutie) and then signal for Michael to join. No one will be sure if Rachel is a wingwoman and who (if anyone) Michael is interested in at that point.

Overall, both women and men are great "wingpeople" when they take a subtle approach to help their friends. That allows the male friend to remain assertive and the female friend to look confident instead of desperate.

What is you matchmaking success rate? How do you define success?

Perfect. I was hoping someone would ask this. I define success in two ways:

(1) Did you get the client what they were looking for? i.e. someone to form a relationship with?

(2) If you didn't get the client what they were looking for, did the client discover and work through issues they had that were blocking them from attracting an ideal partner? For example, a common problem is that people will self sabotage when they meet someone they like (yikes). As long as you're aware it's happening and have a great coach (even if that coach is YOU) you can get through it and move on.

For clients who stay with me 3 to 6 months (approximately 6 to 12 matches) I have a high success rate. For coaching clients the success rate is much higher. I adore all my clients. Just had to add that in here.

I have a "high" success rate

How high is high for a success rate? give us specific numbers.

Ok, let me crunch my numbers so I can give you an honest answer. I promise to do that.

I'm waiting ;)

Wait no longer :)

Overall, the success rate with coaching clients is 90 to 95%. I've only had one client ask for a refund and another discontinue working with me very early on, after I recommended we work together on some of his deeper issues. In retrospect those were clients who wanted a quick fix. I hope in time they will find what they're looking for.

The matchmaking clients are a little trickier to calculate. For folks that stay 3-4 months, the success rate is about 50%, and that jumps to 70% and higher for 6-7 months.

I think part of the reason matchmakers are so sensitive about sharing these numbers is because we can sometimes attract clients who are impossible to please. We don't always know until it's too late and we wonder if those clients "count". I definitely had that problem starting out.

Ultimately, all those numbers should count. At the end of the day, a matchmaker's job is to read people quickly, set the correct expectations, and turn away clients he or she can't help. That's a skill-set in and of itself that takes time to build.

As of late, if I'm unsure of someone, I offer them a match on a trial basis. I judge from their reaction to their first match whether they have reasonable expectations and we're a good fit.

Wow, you're still doing this. Great AMA.

Thank you! It's a pleasure. You all are fantastic. I'll be here another hour or so answering the remaining questions.

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It's great that you want to help your sister! Some general advice:

1. Encourage her with baby steps she can take to reduce her anxiety. It has to be something she can work towards, but not so outside of her comfort zone it turns her off moving forward.

2. Celebrate her successes with her! Truly recognize that baby steps to you were probably leaps and bounds to her.

3. Offer to research professionals in the area that specialize in social anxiety, and that are affordable to her.

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Depends on your circumstance. Why do you spend your free time in front of a computer?

Generally, if you're socially anxious, then I recommend you do anything social that allows you to improve your social intelligence and fluency. See if you can build a support group or community to celebrate your progress.

If you're just ridiculously busy, then you may need to accept this is not the time for you to be meeting people and dating. I recommend you make time for it if you can. Then get your butt off the chair and join dance classes/meetup groups/mixers/online dating. I don't recommend bars or clubs.

Is it a good or bad idea to have certain dealbreakers, or should you always keep an open mind even if you're (for example) a vegan who's on a date with someone who goes hunting? is it better to call it quits early on and save time or dig a bit deeper and find common ground?

Excellent question. I think folks need to have an open mind when it comes to three things: money, height, and overall attractiveness.

Women need to be more forgiving of men who are short and in a lower income bracket than them. Need I say more?

Men need to realize that the media and society at large feeds them this addictive idea of a trophy gf/wife. A common story I hear from men in happy relationships is that they weren't wildly attracted to their partner from the get-go, but with time they were, and couldn't be happier. That blew me away.

p.s. I'm a vegan. How did you know? And I haven't dated a hunter though I did have a housemate who was a hunter.

Do you know if gay dating has any of these problems?

By the way, thank you for a fun and informative AMA :)

You're welcome, thank you for participating.

I wish I had more information on that but it's not my area of expertise :/ ironic considering I live in San Francisco, of all cities, right?

Where were you when I was living in SF..

Close by. Probably at Stanford nerding it out.

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Excellent question. As booming as it can when it's a private practice with a maximum of 12 clients a month. I have yet to do any large-scale efforts (e-books, seminars, retreats, and so forth) mostly because I love the one-on-one matching and coaching relationship. That may be appealing at some point, but for now I enjoy my current practice

Any good dating advice for professional women in their 30's? It seems difficult to meet the right people. Most guys who are into the idea of marriage seem to get married in their twenties. Many get divorced in their forties.

Depends on your situation. Please tell me more if you're open.

The biggest trend I see among professional women in their 30's is that (a) they're too picky on several dimensions that are ultimately not going to make or break a relationship (b) they create a self fulfilling prophecy by focusing the idea that they have slim pickings. Indeed, they may have few options even when they're flexible (e.g. New York), but by focusing on that they induce anxiety and attachment early on in the dating process. Of course, that's a turn off to a potential partner, and masks who they really are, which is a bummer because they're probably amazing.

I have a good friend in NYC who is ridiculously picky. He has to have a degree from an Ivy League AND has to have a masters or PhD, make x amount of money, have a good job, be tall (she's 5'7)...and on and on. I'm afraid she is going to be single for life. Sadly, she is also dying to have babies, which is something guys don't want to think about on a first or second date...

I'm all for knowing what you want, but aren't there limits? Just because a guy went to a state school instead of Harvard doesn't mean he's not intellectual. If he doesn't make what you think is a good salary so what? If he has a good work/life balance and enjoys what he does and is good at it then shouldn't that count for something? I'd rather date a guy with a 8-5 schedule making 50k than a lawyer clocking 80 hours a week and making 100k.

Agreed. There are limits. You hit the nail on the head with your example.

What made your most successful pairings so successful?

What are are the first five things (obvious or not) that you would suggest be established on a first date?

Oh man. Amazing questions. But I could write essays on this. I'll try to be brief.

1. They are either on the same level in different dimensions or they make up for it in another dimension. For example, a woman may want her equal in all dimensions, but if he's exceptionally attractive, she'll overlook potential weaknesses (if for example, he makes less money than her).

An important note: we're all attracted to what's familiar to us. We tend to have a pattern that we need to be conscious of before we can break it (keep that in mind if you have a pattern of toxic relationships).

1. You don't need to establish anything. You're already on the date so I'm assuming you've assessed the basics already (or at least, I hope you have). My biggest tip is don't make it an interview. Just get comfortable. Enjoy it. There's plenty of time to assess and share more sensitive things later.
   

Have you ever worked with someone so shy that you couldnt break them out of their shell? If so, how did that go?

Or on the reverse. Someone so very shy but then boom, made them this very outgoing individual?

Thank you for the thoughtful questions!

We live in a land of quick fixes and the "Boom, total transformation overnight" has never happened, though it's good for Hollywood. Happy to say that the "whoah, look at him go!" definitely has. That's the most rewarding part of my job. It's all about fast progress.

No one is too shy to break out of their shell. I've never had a client who was too shy/awkward to help, except for the aforementioned man with Aspergers.

There is a great video by Michael Hussey on the concept of introversion. There's validity to his overall point that shy people can not and should not use their shyness as an excuse not to contribute. As someone who was shy and aloof growing up I can stand behind his point from direct experience as well. http://www.youtube.com/watch?v=I6zjZBiMs74

Note: The video is a bit of a tough love party. I'm more gentle-love than tough-love in my coaching style. xoxo

Very interesting and refreshingly different AMA. Thank you Yasmine.

What attributes do you personally look for/admire most from a potential couple? Considering that with the matchmaking segment of your job you must get to see a good number of candidates, have you ever kept one for yourself?

Thank you MachiWachi :) I appreciate the compliment!

1) I admire couples who are: communicative, respectful, and completely flirtatious with one another. I've found one commonality across happy couples I know is a willingness and ability to get through difficult conversations without having to win. I'd love to do a full fledged study and analysis on this point.

Let me add that there seems to be a myth out there that mutual respect and love is correlated with the snooze button. Not so. Stay sexy.

2) Haha! I have not kept any for myself. I would be in a lot of trouble if I had, both professionally and personally.

can you explain this to me: I do VERY WELL (not bragging-just telling the truth) when I go out and meet girls in real life yet whenever I try online dating I do horribly

Is there any explanation from a expert like yourself about this phenomenon?

...And I know it's not just me...This happens to quite a few friends of mine

EDIT: btw i know that saying "I do very well in real life" makes me sound like Douchebag McGee but again I'm only being honest

Makes total sense. Happens all the time. And for the record I don't think your question makes you look like Douchebag McGee :)

The problem is that you think you're online dating. You're not online dating. You'e online attracting and promoting. All they see is your resume - not the adorable, sexy, and handsome parts of you that come out naturally in person.

Online attraction is a skill-set. You need to put effort into learning how you come across on a static computer screen. Your profile, pictures, and messages have to market who you are. That's more difficult than it sounds to anyone who hasn't tried online dating.

If you have a cool set of new people you meet regularly, I would say, forget about online dating! That said, the skills you learn (e.g. self marketing and psychology) are definitely transferable to other areas.

Im guessing you have a very attractive, very successful husband?

Aw. A very supportive and handsome boyfriend. He has a heart of gold.

Hitch?

Lol. Sure. Definitely a less sneaky version.

are you will smith?

For the day? I can only dream.

is there any like you in Colorado? What a great service... my job is very good at keeping me away from good places to meet someone.

I hear you. Working can get the better of us though I hope you can make time.

Yes, matchmaking can and should always be a great service. Always make sure you and your matchmaker are on the same page and he/she is out to make you happy.

You know, I don't know any Matchmakers in Colorado. Only NY, Chicago, and Washington DC. Sorry :/

The good news: if you can't find any matchmakers in your area, there are matchmakers who work remotely (including myself, though I'm selective with remote clients and currently work with only one remote client in Chicago. Derek, I adore you!).

what're your feelings/views about the movie HITCH

Will Smith is a fine actor ;) In both definitions of fine.

Shame I don't live in the US. So what do you tell your customers? Like, go to the club?

No. Never. If you're struggling with dating, clubbing is not the answer. There are other environments that are more friendly and low key. Anything from mixers, to singles events, to dance classes, to cafes. Clubs will usually make you very sad if you're trying to build romantic connections.

How many clients want to actually find love, rather than just a sex fling?

In my practice: all except one. Sex-fling-only types generally visit PUA's (Pick Up Artists) rather than coaches and matchmakers.

For the record I don't think there is anything wrong with wanting to explore your sexuality. What I think is missing from the conversation oftentimes is this idea of transparency. There are plenty of men and women out there who want something casual. There's no need to lie and be a generally distasteful person to have a casual sexual experience. Unfortunately, not all PUA's teach with that philosophy. Hopefully we can all work towards creating more transparency in the dating process!

Thanks for the AmA, sent you a pm :)

Got it, will try to reply soon :)

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High pressure question :) I'm teasing. To be honest, uberlad, there is no best life advice. It depends on who you are and what your unique struggles are. You can't go wrong focusing intently on making other people (and nonhuman animals!) happy while loving yourself to the full. Empathy and compassion go a long way when directed towards ourselves and others.

Please stop this "excellent question", "good question" shit. Thanks

Lol. It's in my nature to give positive reinforcement.