Am I Settling? 12 Questions to Ask Yourself

If a prospective partner is into you, do you put on the spectacles of judgment?

Posted Feb 20, 2019

Murilo Folgosi/Pexels
am I settling
Source: Murilo Folgosi/Pexels

"If you haven't found it yet, keep looking. Don't settle. As with all matters of the heart, you'll know when you find it. And, like any great relationship, it just gets better and better as the years roll on."  —Steve Jobs

Are you in a relationship where you suspect you are settling for less than a great love? Well, It's been exactly nine years since Lori Gottlieb published Marry Him: The Case for Settling for Mr. Good Enough—the book that created a firestorm of controversy about settling. So I thought it might be time to revisit the topic but perhaps from a different perspective. That perspective is self-inquiry through journaling.

Settling or Projecting?

It is very often difficult to accept someone who actually wants to be in a club in which we are the only other member. If a guy is into us, (and let’s use guy here because my client story is about a heterosexual relationship) we may tend to get up on our high horses, put on the spectacles of judgment and peer down very critically. You may be wondering, is this man good enough, or am I settling? Could I be doing much better in the love department?

Remember, just like you, each guy has his ugly bits, pimples, and wrinkles, literally and figuratively.  And when you are fighting with him and feel disappointed you are naturally going to feel ambivalent. Even in great relationships, there are times where one partner views the other as not good enough.

So, it is important to be honest with yourself about whether a pattern I call “Not Perfect I’ll Pass” really fits you and is one of your dead-end dating patterns.  In this pattern, you magnify any negative traits the guy has and minimize the positives.  In my years of clinical experience and that of my coaching team, quite often this is a projection of your own unconscious negative beliefs about yourself, about not being good enough.  When we have self-judgments that we are not aware of, where we feel "less than,"  we can function as super-critical b*itches who tend to see their partners in a more negative, picky way.

If this is your relationship tendency you have to work extra hard on appreciating each guy you date and by learning to relate and bring out his Diamond Self (most loving, lovable and empowered identity)  by being your Diamond Self.  That super-critical b*itch is, in most cases, not going to appeal to a really loving guy.  So make sure you are working on ridding yourself of your perfectionism and arrogance. I have seen too many stubborn women hold onto this pattern as if it were a life preserver only to end up in a bitter sea of loneliness.

On the other hand, if a relationship is taking too much hard work, it may be time to cut the bait and move one.  Research on women who choose to be single has revealed many important findings. For example, numerous studies have shown that single women can be as happy and fulfilled as their happily married counterparts. If a single woman has a strong and loving social support system, being in an intimate romantic partnership is not necessary to her well-being.

But if you’re the type that wants a long-term love relationship with a great partner, read on.

12 Questions to Ask Yourself    

You don’t want to choose a guy out of desperation and commit to a relationship where you have “settling” worries more often than not.  To help you decide I’ve put together a list of 12 questions I want you to ask yourself about your partner:

  1. Am I superior to this man?
  2. Do I feel smarter or more clever than him?
  3. Am I more talented?
  4. Is there a complete lack of chemistry with him?
  5. Does he fit in with my social network?
  6. Am I more educated?
  7. Is he too unsuccessful?
  8. Is he too old for me?
  9. Is he too young for me?
  10. Is he too unattractive?
  11. Is he too short?
  12. Is he too boring?

Take Time to Journal Your Answers

Now that you’ve answered the questions ask yourself this: are many of the questions frequently a part of the background conversation you have with yourself or actual conversations you have with your closest friends? 

Disregard those questions that do not elicit a visceral feeling of 'yes' as well as those that are not frequently dished over internally or with your friends.

If you do have a 'yes' answer or persistent nagging question in any of these areas, take time to journal about your thoughts and feelings in that area.  List out all the negatives.  Then list any rebuttal of positive ideas that come up.  End with a list of qualities that your partner has that show that he is more than willing to grow. 

Yeah, I know, he’s too short and can’t grow anymore.  Seriously, don’t let a superficial thing like that, and I mean superficial, stop you from being with a great person.  In my vast clinical experience, love almost always comes in a surprise package.  And, just as Steve Jobs said, it gets better and better over time!

The Story of Rachel

Rachel, a 39-year old social worker was a coaching client in our Love Mentoring program.  She was involved with Mario, a 50-year old who owned a small construction company.  Mario was smitten with Rachel and after eight months wanted to fulfill her dreams of getting married and having children.  But Rachel was ambivalent.  So her coach suggested she journal about her negative and positive feelings about the relationship and whether he was willing to grow.  Here’s what Rachel wrote:

  • Negatives: I feel superior to Mario because he doesn’t have an advanced degree, heck he doesn’t even have a college degree. Sometimes I am embarrassed to introduce him as my boyfriend because he looks like a construction worker, and, much as I hate to admit it, I look down on those guys. He is just not what I thought I would end up with. A doctor, a lawyer, my mother always said. I am actually afraid to introduce him to her! But that pisses me off.

  • Positives: But I feel great when I am with Mario. I don’t even know why. He makes me laugh I guess. And he is so affectionate. Something I never got from Dad. The sex is the best I have ever had. And Mario makes good money. More than me.

  • Willing to Grow: He says he wants to fit in with my family. He even said he would convert.  I took him shopping and he let me give him a makeover. Mario looks great in tight jeans and a jacket! He also wants to build his business by buying properties at auction, fixing them up and selling them at a profit. Looking into the future, Mario could be quite the success.  Even if he is not a doctor. Of course, neither am I.

Rachel has a breakthrough

The journaling process opened Rachel’s eyes to her own superficiality, superiority complex, and fear of her mother’s disapproval. In fact, Mario was crazy about her, willing to grow, and met her soulmate basics. These are the three key criteria for a great partner that  I describe in detail in Love in 90 Days. He was humble, generous, willing to compromise and always wanted the best for Rachel.  Although she didn’t recognize it at first, he was way ahead of Rachel in some fundamental ways including his ability to compromise and his ease with gratitude, two traits that we know form the basis of lasting love in happy couples. When Rachel finally “got it” she knew that Mario was the One.  Over time their relationship got better and better—actually in a way that was beyond Rachel's wildest dreams!

Bottom line

Feeling like you are settling may have more to do with your own insecurities than what you’re thinking about your prospective partner. Take a good close look: At yourself, and at him. This relationship could become your greatest love story.