Matchmaking 101 - Office Hours with Lisa Clampitt

3 Steps To Dating Success: Overcoming Dating Obstacles

dating obstacles listLast week I outlined the top 10 dating obstacles that my clients face. This week, let’s talk about how I work with them to overcome these challenges.

Here is where my job as not only a matchmaker, but as a coach kicks in.  Remember, a matchmaker is more than someone who sets singles up on dates. A major aspect of the job is to support and coach clients every step of the way– including before the dating process begins.

When I first meet with a client, my primary goal is to get to know them as an individual. I encourage openness, and ask that they take an in-depth look at themselves and their life patterns.

No matter their dating obstacle, (workaholic, choosing unavailable partners, out of the dating loop etc.) I begin my coaching by asking clients to do the following:

  • Step 1: Get to Know Themselves

    I ask clients to make a list of 5…

    • Great Qualities: These are qualities they feel particularly good about in themselves. This list will flaunt their desirable attributes. It’s what makes them special. (Ex: positive, kind, loving, loyal, understanding)
    • Difficult Qualities. These are qualities that tend to cause problems in their life. They are the ones they usually try to conceal, especially when meeting someone new. It’s important for clients to be aware of these difficult qualities so they can work to balance them with their great ones.
      (Ex: possessive, needy, negative, fearful, disorganized)

    I also have them look at…

    • Parental/Familial Patterns and Relationships. The way a person thinks about and views relationships has lot to do with the relationships they experienced in their family growing up.  I ask clients to reflect on questions like—Are your parents still together? What is their relationship like now? What was it like growing up in your home? Do you have siblings? Are they married?

    This information can help them see which factors from their childhood are contributing to their current partner choices.

  • Step 2: Get to Know Their Ideal Partner

    Must Haves and Deal Breakers: Lists are exhausting and limiting. The longer and more specific a client’s must-have list is, the more obstacles they are placing in the way of finding a great partner. That being said, I do let clients list their top 5 Must-Haves, and top 5 Deal Breakers.

    There are few things harder than breaking a lifetime of patterns, so be patient!

    BUT— Be sure that these lists are realistic. I don’t let my clients include things like brown hair, dreamy eyes, or hot body on their lists. Those could all go under the category of someone who is attractive to them, and of course they want someone who is attractive to them!

    I also remind clients that flexibility is key in order to see through to a person’s core values and to allow chemistry to creep in. Deal breakers are often relationships stoppers.

  • Step 3: Learn About Their Past Dating Patterns.

    Often singles are not aware that they are attracted to the same qualities in a person over and over because the package they are presented in can look so different.

    I have clients make a list of the old dating patterns that they would like to change on one side of a piece of paper, and on the other side all of the desired qualities they want in a mate.

    This chart will help clarify old patterns that no longer work, and at the same time give them some key attributes to start looking for in order to make better partner choices.

    Remember: There are few things harder than breaking a lifetime of patterns, so be patient!

    Ultimately, the point of going through these three steps is to have a client gain a greater understanding of themselves and the kind of mate they are looking for. The more someone understands who they are, the more they will be able to see clearly who their best match might be. 

    The benefit of going through these exercises with a matchmaker by your side is that a matchmaker will provide encouragement and support throughout the process. With the new information you discover together, singles will be able to enter a new phase of dating—one where more productive strategies are utilized, and the possibilities are endless.

  • Final Match Tip:

    Remember to keep and open mind. You never know what package your soul mate will come in. You might actually be surprised once you open your eyes and look around.  Love can be anywhere if you have the right glasses on!


Interested in becoming a matchmaker or finding one in your area? Feel free to reach out to me —, or visit for more information.