“Is This The Best I Can Do?” & Other Doubts That Are Keeping Me Single

I consider myself to be less of a hopeless romantic and more of a skeptical one. I fall easily and I fall hard, but every time I get swept up in love, I start asking myself questions that always prevent me from settling down with the person who just might be my soulmate.

Will he fit into my life or expand it?

 Everyone has a picture of their ideal self in their minds and I’m no exception. I have goals and dreams and I want to fulfill my potential as a woman and as a human being. It makes more sense to me to date someone who feels the same because otherwise, we’d both be limiting ourselves and we’d end up miserable. I need to be with someone with ambition or it just won’t work.

Do I like his drunk side?

 Obviously I want to marry a guy who’s mature enough to stop drinking before he’s blackout drunk and can no longer see five feet in front of him. Still, I can admit that drinking with someone is a great way to get to know them. I’ve discovered so much about the guys I’ve dated after a few drinks. Hell, I’ve even discovered things about myself! Still, if he gets angry, impatient, violent, or anything else while he’s drunk, I’m not feeling it.

How does he treat the waiter?

 When I quit my corporate job in fashion to write my first book, I waited tables for income. Since then, I’ve developed a real appreciation for people who work in the service and hospitality industry. A crucial indication of someone’s character and values is how they treat their waiter. Is he entitled, selfish, arrogant, impatient, or rude? How he treats the waiter after they forgot his food or put his order in wrong will tell me the answer to all of these questions.

Who are his friends?

 I definitely believe in the saying “you are who your friends are.” Obviously, this doesn’t mean that all your friends should be pursuing the same career or even have all of the same values. Diversity is essential to healthy friendships, but I’m saying that whoever you decide to have strong relationships with should share the attitude, work ethic, and some of the same goals that you do because your support system largely influences the trajectory of your life. Who he surrounds himself with will tell me a lot about who he is and what kind of person he’s becoming, and if I don’t like it, I’m out.

Can I really have it all?

A guy I really liked asked me a question that completely changed how I viewed life. We’d been seeing each other about a month and one night he asked me, “If you had to choose, would you rather have a kid that’s successful or a kid that’s kind?” After arguing with him for a few minutes about why I believed I didn’t have to make that choice because it’s possible to be both, I gave up the debate and finally saw things in the light of day. We defined success very differently. Where he saw a world limited by scarcity, I saw limitless potential. We would never work because he didn’t believe it was possible to have it all and I still do.

Can he handle my dreams?

 I found out a long time ago that because I have big dreams and goals, my life would never be normal. Some people are equipped to handle the creative lifestyle and some just aren’t interested. I love the thrill of adventure, big changes, and thinking outside of the box even if that means sacrificing some luxuries for a while so that I can make my dreams happen in the long run. I know that if I want to do extraordinary things with my life, I won’t be able to accomplish them doing things the ordinary way. This means that there will be times when I’ll need to make sacrifices regarding how I spend my time and money. Being with someone who understands this will make things better for both of us.

Are we going in the same direction?

I definitely don’t think it’s necessary to marry someone in the same profession or even with the same personality. What I do think is important is that my partner wants to go in the same direction that I do.  I know that it simply wouldn’t be smart to be in a committed relationship with someone who wants to settle down in a house in the suburbs, for example, if what I really want is to live in a big city and travel often. Compromise is part of healthy relationships, but not if I’m compromising my heartfelt dreams and ambitions.

Am I “me” when I’m with him?

I’ve dated a few guys that have brought out certain parts of me that I really like, but there hasn’t been a relationship thus far in which I’ve felt empowered and free enough to be my full, most idealistic self. I haven’t had much of a problem getting a date, but what I have had a problem with is giving the best of myself to a date. The lack of transparency on my part has always caused the relationship to dissolve every time. I was expecting a man who was the whole package while I wasn’t a whole package myself. Not good.

Is this the best I can do? 

I have to be careful not to let the endless array of options out there cripple my ability to make decisions by wondering if I’m choosing the best possible one for me. I’ve realized that even though wanting the best life has to offer is a great quality (and I don’t believe in settling for less!), most relationships are only as good as your commitment to them. Of all of the questions I’ve asked, I realized that the most important one is directed at myself. “Is this the best I can do?” is answerable only by first asking “Am I the best I can be?”

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