Image: Felipe Micaroni Lalli

Ultimately, I encourage you to slow down in your life and take the time to observe men in the world around you. You will be amazed at what you begin to see once you start paying attention. There are opportunities and possibilities everywhere—the world is bursting with them and it’s waiting for you to find and act on them! (I know ‘customer’ is a rather unromantic term when it comes to dating, but just bear with me.) Here’s the design thinking model — conceptualized by the design firm IDEO — that you can follow to create opportunities for your dating life:

Step #1: Define the Challange

Step #2: Observe People

Step #3: Form Insights

Step#4: Frame Opportunities

Step#5: Brainstorm Ideas

Step#6: Try experiments

BELOW I WILL DISCUSS EACH STEP AND OFFER YOU EXAMPLES.

Step #1:

Defining the Challenge

Your challenge (should you choose to accept it): As a dater (an enTREPreneurial dater!) your challenge is to create new ideas, possibilities, and opportunities for interacting, engaging, and connecting with men.

Step #2:

Observations

The next step is to observe those people with whom you want to make deeper connections and understand better (men!). You have to observe and listen to men in order to relate to, understand, and connect with them. Without this knowledge, you might end up making assumptions or developing misperceptions about men and thus create solutions in your dating life that lead you in the wrong direction.

I want you to start observing men wherever you go. To create new ideas and perceptions about men, it’s important to observe them in a variety of environments, and where and how they live and socialize.

What are observations?

  • Observations are facts without judgment. Oftentimes, we think we are making observations, but we are inserting our bias into what’s happening.

How does one observe?

  • When observing, focus on the facts; don’t let feelings or opinions get involved.
  • Don’t let your assumptions or preconceived notions about men, which are based on experiences and images from your past, taint your observations. Separate observations from your interpretations (or you may miss something).
  • Observing and collecting facts without immediately judging those facts is difficult, but it’s critical to developing useful insights. Just record the facts and avoid temptation to interpret the facts for now.
  • Look at body language and facial cues to add more context to what you are observing. But don’t interpret what you see; just observe and record.
  • Also, remember to keep an eye out for things that surprise you.

Don’t just observe one place—observe different men in action in different spaces. Tell me what you see men doing, how they are behaving, what you hear them saying. Just the facts!

Here are a couple of ideas you can choose from with regard to observing men:

Places:

  • Cafes/restaurants
  • On the street/sidewalk
  • At bars/clubs
  • At stores or malls
  • At the park/dog park
  • At events around town
  • At food markets
  • At parties or events
  • At family gatherings
  • On unscripted TV shows
  • In videos (wedding videos in particular can be illuminating)

With whom:

  • Observe them alone
  • Observe them with family
  • Observe them with friends
  • Observe them with animals/pets
  • Observe them hitting on and flirting with women
  • Observe them with girlfriends/wives
  • Observe them talking on the phone
  • Observe them with service personnel

Here are three examples of different types of very simple observations:

  1. Observation: Two men at a bar are talking with each other about different kinds of beer and the beer-making process. They talk about going to the local beer festival next month.
  1. Observation: A single man is alone at a bar despite many women around him. He pulls out his phone and starts checking Facebook.
  1. Observation: A woman in a café comments on something a man at the table next to hers is eating. Man smiles and answers. Man and woman begin conversation. Man asks questions, cracks jokes.

Step #3:

Form Insights

  • From your various observations, you will form educated, useful insights about men.
  • It doesn’t mean your insights will be 100% correct, but your insights will help you develop and refine your ideas about how men think, feel, and live.

Examples of creating insights from my observations:

  1. Observation: Two men at a bar are talking with each other about different kinds of beer and the beer-making process. They talk about going to the local beer festival next month.
    1. Insight: Men enjoy bonding over beer.
    2. Insight: Men love talking about and learning about beer.
  1. Observation: A single man is alone at a bar despite many women around him. He pulls out his phone and starts checking Facebook.
    1. Insight: Although he might enjoy a woman saying hello and chatting, he is embarrassed because people might think he’s alone and therefore a “loser” or “creepy.”
  1. Observation: A woman in a café comments on something a man at a nearby table is eating. Man smiles and answers. Man and woman begin conversation. Man asks questions, cracks jokes.
    1. Insight: Men love when women approach.
    2. Insight: Men are looking to meet women everywhere.
    3. Insight: Men aren’t that scary and intimidating or think they’re better than women, and, in fact, may be scared to come up to us.

Step #4:

Framing Opportunities

What does it mean to frame opportunities?

  • It means you move from the current reality to future possibilities.
  • Opportunities are the launching pad for ideas and possibilities.
  • It helps to frame your opportunities by starting with: “How might I…?”

Examples of framing opportunities from my insights:

  1. Observation: Two men at a bar are talking with each other about different kinds of beer and the beer-making process. They talk about going to the local beer festival next month.
    1. Insight: Men enjoy bonding over beer
    2. Insight: Men love talking about and learning about beer
    • Framed opportunity: How might I connect with men over beer?
  1. Observation: A single man is alone at a bar despite many women around him. He pulls out his phone and starts checking Facebook.
    1. Insight: Although he would enjoy a woman saying hello and chatting, he is embarrassed because people might think he’s alone and therefore a “loser” or “creepy.”
    • Framed opportunity: How might I engage with a man when he is standing alone at a bar?
  1. Observation: A woman in a café comments on something a man at a nearby table is eating. Man smiles and answers. Man and woman begin conversation. Man asks questions, cracks jokes.
    1. Insight: Men love when women approach.
    2. Insight: Men are looking to meet women everywhere.
    3. Insight: Men aren’t that scary and intimidating or think they’re better than women, and, in fact, may be scared to come up to us.
    • Framed opportunity: How might I approach men and engage with them more often in a friendly way?
    • Framed opportunity #2: How might I go into my dates and interactions differently with men now that I see them differently?

Step #5:

Brainstorm Ideas

How do you brainstorm ideas?

  • A productive brainstorm requires you to give yourself permission to think without constraints. It allows for silly or impossible ideas so as to spark relevant and reasonable ones.
  • Brainstorm rules: no criticism, no order to getting ideas out there, no “buts”, get lots of raw ideas out there so you can experiment and test them.

Examples of brainstorming ideas from my framed opportunities:

  1. Observation: Two men at a bar are talking with each other about different kinds of beer and the beer-making process. They talk about going to the local beer festival next month.
    1. Insight: Men enjoy bonding over beer.
    2. Insight: Men love talking about and learning about beer.
    • Framed opportunity: How might I connect with men over beer?
  1. Join beer-related groups on Facebook or meetup.com;
  2. Attend beer festivals, new beer restaurant openings, beer-related events (a new brewery debuting their beer flavors);
  3. Attend beer workshops or classes to gain more knowledge about beers and to meet men;
  4. Ask a man his opinion on different beers at a bar, market, or liquor store;
  5. Ask a man at a bar what kind of beer he’s drinking and the difference between that beer and other beers.
  1. Observation: A single man is alone at a bar despite many women around him. He pulls out his phone and starts checking Facebook.
    1. Insight: Although he would enjoy a woman saying hello and chatting, he is embarrassed because people might think he’s alone and therefore a “loser” or “creepy.”
    • Framed opportunity: How might I engage with a man when he is standing alone at a bar?
  1. Position myself closer to him to make it easier for him to say hello;
  2. Smile at him and give sustained eye contact when he looks up;
  3. Comment on his phone;
  4. Ask if he’s waiting for his friends;
  5. Ask if he‘s ever been to the bar and/or if he likes the bar;
  6. Make a playful joke about him standing alone.
  1. Observation: A woman in a café comments on something a man at a nearby table is eating. Man smiles and answers. Man and woman begin conversation. Man asks questions, cracks jokes.
    1. Insight: Men love when women approach.
    2. Insight: Men are looking to meet women everywhere.
    3. Insight: Men aren’t that scary and intimidating, and, in fact, may be scared to come up to us.
    • Framed opportunity: How might I approach men and engage with them more often in a friendly way?
    • Framed opportunity #2: How might I go into my dates and interactions differently with men now that I see them differently
  1. Consider starting more conversations with men I meet out and about;
  2. Relate to men about what they are doing—I don’t have to create an experience, I can simply relate to what they are currently experiencing (if a man orders a ham sandwich, I can comment on his choice or ask him a question about it);
  3. Smile more at men when out and about and make eye contact to encourage them to come up to me.
  • Brainstorm ideas for framed opportunity #2:
  1. Repeat mantra before dates that men are not better or worse than me; they are my equals. I am not above or below them, and many of them are looking for the same things as me;
  2. Try asking them different questions than what I’m used to or talk about me in a different way than I’m used to (don’t focus on my job but talk more about passions and interests).

Step #6:

Try Experiments

Why try experiments?

  • Experiments help us answer specific questions in order to evolve ideas. Multiple experiments may be necessary.

How do I experiment?

  • Start testing out the ideas that were brainstormed.
  • You may need to try experiments with multiple men to test your ideas. You may need to try different approaches. Maybe some men respond well, others do not, but if your experiment works with some, it opens you up to the notion that this idea can work and gives you courage to keep trying.
  • Continue to experiment and refine the way you test your ideas. Example: Maybe I start by saying hello to a man. Then I refine that idea to commenting on something he’s doing or a shared reference in our environment. Then maybe I do this with men who aren’t typically my “type”. Then maybe I work on simply smiling and sustained eye contact to get a man to come to me.
  • What questions do you still need answered so your idea can succeed? Example: Do I need to ask a few men if they like when a woman approaches or starts a conversation with a man to know that my insight was right and to therefore give me the confidence to go do it? (More on talking to and getting feedback from men in chapter 11.)

With each of the examples YOU come up with when you go through the design thinking process, the same steps apply.

So get out there and start design thinking your way to love!

Have you heard? My book Skin In the Game: Unleashing Your Inner Entrepreneur is getting rave reviews from single women, other dating coaches, and matchmakers. Pick up your copy today! And while you’re at it, grab the Workbook for Skin In the Game (which can used with the book or on its own).

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