Dating at any age is fraught with emotions, second guesses and more than one instance of utter and complete self-doubt. Whether you've never dated, are newly divorced or are just coming out a long period of being single, here are five questions you should ask yourself before you jump into the dating game. Grab a pen and paper and spend some time doing some self-reflection.

Am I happy & content?

My apologies for invoking one of the most dreaded questions possible, but it's completely true. Being happy and content with yourself is key to being able to date in healthy way. A healthy dating life is one where YOU always have a bead on who you are and knowing at your core that your happiness is not dependent upon anyone's opinion of you but your own.

Do I know what I want out of dating?

Dating is not the magic bullet to cure loneliness, depression or low self-esteem, nor is it a ticket to bliss. Dating is like tending bamboo stalks that you're hoping to weave together – it takes time and attention. What do you want your bamboo dating garden to look like? Do you have enough time and patience to water it and watch it grow?

Am I clear in what kind of partner I want in my life?

We date because we are social animals. We congregate together, we build communities, we create art and sport with the intent that the human race will go on. If you're not clear on the kind of person that you want to date, you will have trouble setting boundaries with people who don't meet your expectations. If you've never thought about it, ask yourself this scenario question: if you've just had a really rough day, what would you want your significant other to do? Help you? Leave you alone with your thoughts? Buy dinner? Throw in a DVD? Sit down and talk with you about what happened? Your answers may surprise you, but it's a worthwhile exercise to hone in on key personality traits you want to look for.

What positive aspects do I bring to a relationship?

One thing that we human beings aren't very good at is extending compassion and kindness to ourselves! Take a few moments to sit down and write out all the great things about you. And if you have a negative thought, like “I'm too self-critical,” for example, then write two ways that trait is a positive. For example, in answer to that I would say “I'm very introspective and I love to find out ways that what I perceive as my negatives can be turned into positives.”

Do I have patience to find who I'm looking for?

Dating isn't a sprint – it's a marathon. More often than not, the one thing that dooms so many daters is patience. One person wants to move faster than another, or someone who isn't quite a fit for you is in your life and you don't really know how to tell them to go, so you just stay. Sound familiar? It's that way for a lot of people. Know what you're looking for and persevere.

Be happy, be clear in what you want and step forward.