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What Online Dating
Teaches Us about
Personal and
Professional
Relationships
Steve Dean
Online Dating Consultant
StevenMDean
● “Full-stack” online dating
consultant
● Strategic advice for online
daters across 15+ cities
● Special advisor to intern...
Clients and Friends
WHAT is Dateworking?
Formally, Dateworking is an independent consultancy run by online
dating consultant and career matchm...
What Online Dating Teaches
Us about Personal and
Professional Relationships
Online dating is getting popular
THERE ARE OVER 4,000
DATING SITES
Here’s what
dating looks
like today.
Expect a
bit of
humor…
…and a bit of
horror. It is
the internet,
after all.
What Is Dating?
going out for dinner?
seeing a movie?
drinking at a bar?
meeting to talk about a startup?
meeting two peop...
What Is Romance?
love affair?
emotional attachment?
is sex/physicality needed?
but asexuals can be romantic!
Relationship ...
What Are Relationships?
Defined by longevity?
By number of intertwined life variables?
By active consent?
By trust?
By con...
What Is Cheating?
Lying to a partner?
Extended eye contact with someone else?
Touching someone else’s hand with…intent
Sex...
Sex is complicated
Full list available here: http://thatotherpaper.com/files/Yes_No_Maybe.pdf
Can you identify which of
these might be count ...
Sex…with WHOM?
Sex with men?
Sex with women?
Sex with former men / former women?
Sex with people who don’t identify with a...
IF PEOPLE WEREN’T SO COMPLICATED
THAT’D BE GREAT
And RELATIONSHIPS can be
the most complicated
…and we don’t even know ourselves
SO HOW DOES ONLINE
DATING HELP?
SO HOW DOES ONLINE
DATING HELP?
Self
Analysis
Finding
Matches
Filtering/Ev
aluating
Meeting
Up
Relationship
SO HOW DOES ONLINE
DATING HELP?
Self
Analysis
Finding
Matches
Filtering/Ev
aluating
Meeting
Up
Relationship
15 minutes
Thousands of dating sites exist
to put compatible people in
front of us within minutes.
Online dating can give us the
right people to connect with…
But it doesn’t teach us HOW to
connect with them.
That part is...
So How Do We Connect with
One Another?
Connection Requires Empathy
https://www.youtube.com/watch?v=1Evwgu369Jw
Empathy is what drives human
connectedness. It’s what
brings us together.
To Understand Others, We Must
Understand Ourselves First
See the guide’s explanation and more details here:
Why Excel Shee...
BUILDING
RELATIONSHIPS
There is no one-size-fits-all for
relationships.
In networking, it’s the same.
Today’s client is tomorrow’s
cofounder.
So how do we optimize for
the ______________
relationships?BEST
LONGEST
MOST AUTHENTIC
HIGHEST IMPACT
MOST MEMORABLE
Let’s bring referrals back
“Dateworking”
a philosophy for modern
connectedness
Principle #1
Everyone is their own
protagonist.
Help them succeed, even if
it’s not with you.
Principle #2
Respect boundaries.
Seek depth over structure.
Principle #3
Everyone has rough patches,
but time is your friend.
Trust in people’s long-term
potential.
Everyone has a zone of
genius.
Take as much pride in others
as this farmer takes in his
onion.
Contact Steve Dean
For a dating consultation
steve@dateworking.com
http://dateworking.com
For job search / hiring help
ste...
APPENDIX:
ONLINE DATING
TACTICS
Photos Are Essential
First, read this: Don’t Be Ugly By Accident
Next, read this: We Tested 11 Different Male Profile Pict...
Profile Design
Structure
INTRO – who you are and what you’re up to right now, in 2 sentences
MIDDLE – your favorite things...
Messaging
First, read this:
https://coffeemeetsbagel.com/blog/index.php/best-date-tips/best-
dating-tips-for-him/4-ways-i-...
Know Thy Market
Average FEMALE online dater’s inbox:
“Hey guuurl, let’s get it on”
“Ur ugly”
“Hello madame, I can’t help b...
Optimal Messaging
Strategy
Declare interest
e.g., “hey, you seem awesome, and you mentioned x, which i
absolutely agree wi...
Sample Message
Note: for this kind of message to be effective, your profile has
to be SAFE, AUTHENTIC, AND ACCURATE. Nothi...
What Kind of Dates to
Propose?
Make your dates FAILURE PROOF
Your guiding light should be what you’re already passionate a...
What to Talk About on Dates?
See my list of Questions to Spark Authenticity
The list includes:
“Would you like to be famou...
These articles are unbelievably insightful when it comes to how we approach
dating, communication, and compatibility. Read...
Considering Non-Monogamy?
Monogamy vs. Polyamory - http://goo.gl/tuYVL1
Types of Nontraditional Relationships - https://go...
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
A Complete Guide to Modern Dating & Relationships
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A Complete Guide to Modern Dating & Relationships

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I've condensed 5 years of work consulting for individual online daters of all ages, genders, races, and orientations across 15 cities into a single comprehensive guide for navigating how to date online and offline as well as how to form strong and sustainable relationships, turning every person you meet into a lifelong confidante who can ensure that your life is full of amazing, fulfilling connections.

Published in: Self Improvement
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A Complete Guide to Modern Dating & Relationships

  1. 1. What Online Dating Teaches Us about Personal and Professional Relationships Steve Dean Online Dating Consultant StevenMDean
  2. 2. ● “Full-stack” online dating consultant ● Strategic advice for online daters across 15+ cities ● Special advisor to internet dating companies Meet Steve Dean WHO is Dateworking?
  3. 3. Clients and Friends
  4. 4. WHAT is Dateworking? Formally, Dateworking is an independent consultancy run by online dating consultant and career matchmaker Steve Dean, which offers: Dating Help for Individuals Online dating – profiles, photos, messaging, date ideas Personal development – self-image, intimacy, communication, personal branding Relationships – asking out, opening up, saying no, breaking up Dating Help for Enterprise Business Development – Steve’s advised: OkCupid, CoffeeMeetsBagel Product Strategy – Steve’s advised: TrintMe, Aclipsa, Manhunt Competitive Strategy – Steve’s advised: MiuMeet, iHookup, AnastasiaDate Informally, Dateworking is a philosophical outlook on the increasing convergence of dating and social networking, two formerly separate worlds
  5. 5. What Online Dating Teaches Us about Personal and Professional Relationships
  6. 6. Online dating is getting popular
  7. 7. THERE ARE OVER 4,000 DATING SITES
  8. 8. Here’s what dating looks like today.
  9. 9. Expect a bit of humor…
  10. 10. …and a bit of horror. It is the internet, after all.
  11. 11. What Is Dating? going out for dinner? seeing a movie? drinking at a bar? meeting to talk about a startup? meeting two people to explore a new park? Romantic intent? What is romance?
  12. 12. What Is Romance? love affair? emotional attachment? is sex/physicality needed? but asexuals can be romantic! Relationship intent? What is a relationship?
  13. 13. What Are Relationships? Defined by longevity? By number of intertwined life variables? By active consent? By trust? By contract, e.g. marriage? By sexual activity? By falsifiability? By cheating? What is cheating?
  14. 14. What Is Cheating? Lying to a partner? Extended eye contact with someone else? Touching someone else’s hand with…intent Sexting someone else? Sex with someone else? What is sex?
  15. 15. Sex is complicated
  16. 16. Full list available here: http://thatotherpaper.com/files/Yes_No_Maybe.pdf Can you identify which of these might be count toward sex? Toward cheating?
  17. 17. Sex…with WHOM? Sex with men? Sex with women? Sex with former men / former women? Sex with people who don’t identify with a gender? Sex with intersex people?
  18. 18. IF PEOPLE WEREN’T SO COMPLICATED THAT’D BE GREAT
  19. 19. And RELATIONSHIPS can be the most complicated
  20. 20. …and we don’t even know ourselves
  21. 21. SO HOW DOES ONLINE DATING HELP?
  22. 22. SO HOW DOES ONLINE DATING HELP? Self Analysis Finding Matches Filtering/Ev aluating Meeting Up Relationship
  23. 23. SO HOW DOES ONLINE DATING HELP? Self Analysis Finding Matches Filtering/Ev aluating Meeting Up Relationship 15 minutes
  24. 24. Thousands of dating sites exist to put compatible people in front of us within minutes.
  25. 25. Online dating can give us the right people to connect with… But it doesn’t teach us HOW to connect with them. That part is on us.
  26. 26. So How Do We Connect with One Another?
  27. 27. Connection Requires Empathy https://www.youtube.com/watch?v=1Evwgu369Jw
  28. 28. Empathy is what drives human connectedness. It’s what brings us together.
  29. 29. To Understand Others, We Must Understand Ourselves First See the guide’s explanation and more details here: Why Excel Sheet Relationships Work Better http://goo.gl/PPzh0p
  30. 30. BUILDING RELATIONSHIPS
  31. 31. There is no one-size-fits-all for relationships.
  32. 32. In networking, it’s the same. Today’s client is tomorrow’s cofounder.
  33. 33. So how do we optimize for the ______________ relationships?BEST LONGEST MOST AUTHENTIC HIGHEST IMPACT MOST MEMORABLE
  34. 34. Let’s bring referrals back
  35. 35. “Dateworking” a philosophy for modern connectedness
  36. 36. Principle #1 Everyone is their own protagonist. Help them succeed, even if it’s not with you.
  37. 37. Principle #2 Respect boundaries. Seek depth over structure.
  38. 38. Principle #3 Everyone has rough patches, but time is your friend. Trust in people’s long-term potential.
  39. 39. Everyone has a zone of genius. Take as much pride in others as this farmer takes in his onion.
  40. 40. Contact Steve Dean For a dating consultation steve@dateworking.com http://dateworking.com For job search / hiring help steve@jobsuitors.com http://jobsuitors.com Read/Follow @StevenMDean on Medium, Twitter Friendship-First Approach to Dating - http://goo.gl/ARfh2I 5 Secret Tools for Superconnectors - https://goo.gl/e4r6lI How to Land a Job at a Hot Startup - https://goo.gl/AFQCZo
  41. 41. APPENDIX: ONLINE DATING TACTICS
  42. 42. Photos Are Essential First, read this: Don’t Be Ugly By Accident Next, read this: We Tested 11 Different Male Profile Pictures and This Is What Happened Photo guidelines. People will ask themselves: Are you real? Are you approachable? Do you have friends? Will you kill me? Can you interact well with animals/children? Can I envision myself coexisting with you in the world you’ve shown me a glimpse of?
  43. 43. Profile Design Structure INTRO – who you are and what you’re up to right now, in 2 sentences MIDDLE – your favorite things to do in the city CLOSING – describe your ideal person, so that person could read your profile and think “oh, this is totally speaking to me!” Best Practices Let your personality show. specifically, show, don’t tell. rather than saying “i have a great sense of humor,” show that humor through how you word something Create the world you want this person to envision sharing with you Keep your audience in mind. Understand your target market. If you want a serious relationship, your profile should read as “I am the type of person who is capable of a serious relationship.”
  44. 44. Messaging First, read this: https://coffeemeetsbagel.com/blog/index.php/best-date-tips/best- dating-tips-for-him/4-ways-i-improved-the-way-i-message- women/ Top Tips The people you want to date are real people. So treat them that way. Be upfront about what you’re interested in. Don’t waste your own time. Put yourself in the reader’s shoes before sending the message. Imagine how they’re going to perceive it.
  45. 45. Know Thy Market Average FEMALE online dater’s inbox: “Hey guuurl, let’s get it on” “Ur ugly” “Hello madame, I can’t help but love your eyes. Might I offer to pay you for a ‘beneficial arrangement’?” Good message Good message 2 Shitty pickup line Average MALE online dater’s inbox: Empty. Literally. Or, at best: “Hey, I like your eyes!”
  46. 46. Optimal Messaging Strategy Declare interest e.g., “hey, you seem awesome, and you mentioned x, which i absolutely agree with” Add Value e.g. “you said you like finding new coffee shops. have you tried coffee shop xyz on pdq street? I saw that it had awesome reviews on yelp and I’ve been meaning to go” Call to Action e.g. “hey, i’m planning to check out coffee shop xyz next wednesday around 5p. you should totally come. we can see if they’re any good at cold brews. let me know if you’re free!”
  47. 47. Sample Message Note: for this kind of message to be effective, your profile has to be SAFE, AUTHENTIC, AND ACCURATE. Nothing creepy!
  48. 48. What Kind of Dates to Propose? Make your dates FAILURE PROOF Your guiding light should be what you’re already passionate about. Ask yourself: What would you already be doing if this person weren’t around? What things excite you? What activities capture and showcase your essence? My recommendations Side-by-side walk-and-talks through new neighborhoods & new parks Activity-based “chapter dates” that allow for increasing intimacy/connectedness, but also opportunities to part ways if needed Chapter 1: coffee to get fueled up Chapter 2: walk across a cool bridge and check out a new set of city views Chapter 3: food at a street festival Chapter 4: scavenger hunt – try to discover 10 unique things
  49. 49. What to Talk About on Dates? See my list of Questions to Spark Authenticity The list includes: “Would you like to be famous? In what way?” “What are you most afraid of losing?” “What is the nicest thing you have done for a complete stranger?” “Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?”
  50. 50. These articles are unbelievably insightful when it comes to how we approach dating, communication, and compatibility. Read each of these in order and then read my 5 corresponding tactical guides that follow for help implementing the articles' content. 1. How We End Up Marrying the Wrong People - http://goo.gl/eQFafy 2. Love Is Not Enough - http://goo.gl/nblM0S 3. Why We Fuck - http://goo.gl/rzU6Ct 4. There's No Such Thing As Everlasting Love: Micro-moments of Positivity Resonance - http://goo.gl/Nf2aGK 5. Casual Love - http://goo.gl/D0on1m 6. The Advanced Metrics of Attraction - http://goo.gl/bMwx1v 7. How jealousy works - http://goo.gl/dq8laQ 8. 10 Realistic Rules for Good Non-Monogamous Relationships - http://goo.gl/sqaxH5 9. The 9 Most Overlooked Threats to a Marriage - http://goo.gl/WqXbem 10. Cancel Marriage: Merav Michaeli at TEDxJaffa - https://goo.gl/mHjl8y 11. Love Undetectable: Why Friendship Is a Greater Gift Than Romantic Love - http://goo.gl/V7VjdN Action Steps Written by Steve Dean The Friendship-First Approach to Dating - http://goo.gl/ARfh2I The Friendship-First Approach to Dating, Part 2: http://goo.gl/tCYCV0 How do I have the “Are We Exclusive” talk? - http://goo.gl/xFI86K How to Say “No” Without Lies, Flaking, or Fadeaways - http://goo.gl/8w5fRm Why Excel Sheet Relationships Work Better - http://goo.gl/PPzh0p Add This Line to Your Tinder Profile Right Now - http://goo.gl/yGWcFU High-Impact Readings
  51. 51. Considering Non-Monogamy? Monogamy vs. Polyamory - http://goo.gl/tuYVL1 Types of Nontraditional Relationships - https://goo.gl/LRAJ0z How to Handle Jealousy - http://goo.gl/ZkFpnJ The Ethical Slut, a treatise on non-monogamy - http://goo.gl/XsuurC There's No Such Thing As Everlasting Love - http://goo.gl/4n4MFI Casual Love - http://goo.gl/W6L2no Evolutionary Roots of Nonmonogamy - http://goo.gl/cyaEG0 How We End Up Marrying the Wrong People - http://goo.gl/47ZPmV 10 Realistic Rules for Good Non-Monogamous Relationships - http://goo.gl/ZUwuQ7 How to Treat Non-Primary Partners Well - http://goo.gl/y2Pw5l Care and Feeding of Polyamorous Secondary Relationships - http://goo.gl/hHNYnT Having a Polyamorous Relationship with a Monogamous Partner - https://goo.gl/Ii8B4x Endearing comics about non-monogamy - http://goo.gl/7nf5Fg

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