Dating Smart

Dating with new eyes for those who want a long term monogamous relationship.


Give it time

Probably the number one, most helpful thing you can do,when dating and you’re trying to decide if the person you are dating is someone you want to spend the rest of your life with is to give it time. Time is essential. In the beginning of relationships, most people go through what we call an enmeshment phase where you feel really bonded with the other person. This feels really good but it can also interfere with good decision making. You may not really be seeing who the other person is when you’re caught up in the newness of the relationship. What’s interesting is that sometimes, it may not even be all that great because the other person is honest enough to tell you– “this is who I am, and I don’t have a very good track record and these are my tendencies, these are the things that I like to do and these are my habits, and I’m not interested in working on these things or changing anything about myself”—but during enmeshment–you won’t hear it. Then 5 years down the road, you’ll think the person has changed, but really haven’t. You just weren’t willing to see or hear what was there from the very beginning .


Take time to know yourself and understand yourself. There is no such thing as ” the one.” Believing that there is “the one” somewhere out there and that you’ll be “complete” person when you meet your “soul mate” just slows down your own self-work.

Do you know how your family of origin shaped you? Are you really familiar with your own tendencies? If you are, that’s great. Do you know how to manage your tendencies in a healthy way within a relationship? If you have some fear of rejection or abandonment issues, and you know this, that’s great. Do you know how this impacts relationships that you tend to get into? Are you familiar with shame and how this affects your ability to connect with others?

Your first and primary relationship is the one you have with yourself. If you have a list of qualifiers that you want your potential partner to have, maybe check in with yourself and see if you have those qualities first. Develop the qualities in yourself before seeking those qualities in others. Are you insightful enough to offer the person you are dating reasons that your past relationships didn’t work out? If you don’t understand why past relationships didn’t work out or you tend to put the blame on your ex partners, then you’ll repeat your old patterns without this insight.


Self-differentiation is the ability to separate your own intellectual and emotional functioning from that of the family (Bowen, Family Systems Theory). If you didn’t learn this in your family (hardly anyone does), then you won’t relate this way in a romantic relationship either.


Are you codependent? Do you look for someone else to rescue you and resolve your issues? It can feel good to have someone come swooping in and rescue you but other people aren’t here to fix us or rescue us from what are essentially unresolved childhood issues. You can learn to take responsibility for your behavior and make healthy changes. Focusing on developing healthy self-esteem, taking responsibility for your own feelings, and working through past disappointments will go a long way tot help you self-differentiate.


On the flip side, are you counterdependent? Do you try to resolve others’ issues for them but then get accused of not doing enough? Counterdependents tend to be love avoidants. You probably attract needy partners. If you want a somewhat balanced, healthy relationship, then watch out for needy, dependent, hurt rabbits. Instead, investigate why you have the tendency to be attracted to those who need rescuing. Counterdependents rescue and run. You can learn to not be love avoidant by engaging in more emotionally intimate, vulnerable dialogue and behavior when your tendency is cut-off or shut down.

Get to know the person you are dating (and get to know yourself)

A very important question you can ask someone who you’ve been dating for a while and you’re considering a more serious, long term relationship with, is:

In what areas do you see yourself wanting to make some improvements? Looking back, how do you think you could’ve handled a past relationship differently for a better outcome?

If the person looks at you with a blank stare or gets defensive or puts all the blame on another person, you better run like Sea Biscuit, because this isn’t indicative of someone who is emotionally developed. This isn’t a person who knows him or herself or really understands their own core issues. If the person seems open and motivated for personal growth, that’s different. You want a long term partner to be motivated, open and humbled enough to create a heartfelt, deep connection. Healthy self-esteem isn’t grandiose.

Don’t be paranoid, but do be aware of personality disorders. One of the best and simplest books on recognizing personality disorders is by Gordon Livingston and it’s called, How to Love. This is an excellent guide on choosing wisely.

Side note: Ask yourself the same questions above and be willing to share how you’ve changed and grown. Are you motivated to do your own personal work?kal-loftus-673614-unsplash

When someone tells you who they are, believe them

If someone is telling you and showing you who they are, believe them. You don’t have to get mad about it. Be thankful that someone shows you who they are early on while you’re dating, or that you recognized it and be grateful that you found out before getting into a more long term relationship. Ask yourself, what is it about you that attracted you to this person? There’s always an opportunity to learn something more about yourself.

No matter how badly you think getting married or having children will cause someone’s character to change, it won’t. Byron Katie has been quoted as saying: If you want reality to be different than what it is, you might as well try to teach a cat to bark. If you try to teach a cat to bark, and it inevitably doesn’t, because it’s a cat and cat’s don’t bark, and then you get mad at the cat, just know that this isn’t the cat’s fault. The cat is being a cat.

If you’re dating someone and they tell you that they don’t want to stay in one place very long and they like to travel for work, or they don’t want to get married or whatever…and you want to be with someone who works locally because you want to get married and raise a family, listen to what the other person is telling you. It’s not about your worth if someone else has a different view of what will be fulfilling for them. There is also an opportunity for you to investigate why it is, for example, you tend to be attracted to someone who needs space or distance when you don’t. This goes back to really understanding your family of origin and how your experiences a long time ago affect your choices in dating.

Why do I choose who I choose?laula-the-toller-567341-unsplash

You’d think it would go without saying, but ask yourself questions about what attracts you to another. If you’re unfamilar with the theory that we marry our childhood issues, then invest some time in therapy understanding how your family influences your choices in romantic relationhips. Being good-looking isn’t enough. Attraction is definitely important and necessary, but if you can’t get past the superficial and can’t come up with any other qualities that attract you to someone else besides good looks, then this is a big red flag, if you are ultimately wanting a long term relationship with this person. Because, if we’re lucky we’re going to get old, and good looks will fade, and you’ll want qualities that are more than skin deep.

Dating smart is really about becoming a whole healthy person. You could ask yourself this question: Would I want to date me? If not, then why not? There’s your starting point.