Adapted from a recent online discussion.
If you're honest with yourself, you shouldn't need a checklist
Anonymous: From your many years of advising people, what do you think are the main things that make a marriage happy and lasting?
Carolyn: (1) Saving marriage for when you're actually mature, and not just when you think you are; it's really hard to contribute your full share if you're off getting high on your own stuff. How do you know the difference between believing and knowing? Two giveaways are a sense of urgency, or a sense of shame about your choices or circumstances. If you're making your case to people, then you're not ready.
(2) Marrying someone with whom you can be yourself, good and bad, but who inspires the good.
(3) Being mutually free with praise, stingy with criticism and honest about things that are uncomfortable to talk about — not because you have to, but because you believe in each other.
(4) Never taking your spouse for granted. Either you share in everything from lofty ideals to the daily workload, willingly as a loving gesture to each other, or you're asking to be unhappy.
(5) Having the good luck to meet someone who forgives you when you fall short, who's just grateful you tried to live up to your promises (and promise).
(6), (7), (8) Laughing together.
(9) Shared sexual needs, or shared openness to dealing with mismatched sexual needs.
(10) Not needing checklists. I could add to this one all day, but, ultimately, relationships either work, or you're forcing the issue — the foundation for endless mistakes.
Crossing the friend line may not be the wisest move to make
Washington: My best friend from high school is a great, upstanding guy. I have no feelings for him, but after countless failed relationships, I'm beginning to think he has the qualities I'm looking for. Is it a bad idea to experiment with where this relationship could go? I assume the main reason I don't have feelings for him is that I've never allowed myself to look at him this way.
Would pursuing something be a waste of time?
Carolyn: For his sake, please test your I'll-develop-feelings-if-I-want-to theory ONLY in the privacy of your own mind. And even that is probably premature (which I'll get to in a second).
The risk here is not of wasting your time. The risk is of laying waste to him.
Obviously, it's possible he's not into you, either, making devastation unlikely. But just in case he harbors some interest, you owe it to him to approach him on something a lot more solid than a whim. In fact, the only legitimate motivation for such an "experiment" is a pressing desire to spend more time with him. I doubt you'd want a guy to ask you out just because he's tired of getting dumped and you happen to look like a safe bet.
As for the timing: Even if you really do have a pressing desire to be with this friend, the answer to "countless failed relationships" is never to displace the wreckage with a shiny new opportunity.
Instead, take a careful accounting of where you are emotionally and how you got there, and then to see what you can do to find fulfillment on your own. Even the best guys will have rocky relationships with you if you're not on solid footing yourself.