Thinking of Dating Again? How to Start Doing & Stop Thinking

  “Dating After Divorce” receives this week’s Innovative Match (IM) Recognition Award! Recommended by Cassie & the IM Editorial Team, this article covers David A. Anderson, Ph.D.’s personal research, along with others’ work, on how individuals recovering from a long-term relationship can get back into “dating mode” and expand their social circle.

             Anderson describes the ritual of dating as “daunting” for those who have lost a loved one, gone through a divorce, or who simply need to get back out there and find the right person. Divorce, among other bad experiences, can leave your self-esteem, self-value and “social price” damaged. This makes it all too easy for people to fall back into old dating patterns and partners. What many find most disconcerting is that the singles’ arena looks like a droplet compared to the ocean available during their younger years.

Cassie agrees psychology plays a big role. However, the biggest hurdle is knowing how to date and what to do to get back out in the arena. Here the IM Matchmakers discuss the best advice to help you stop thinking and go start dating again.


1. Personal Tree of Life

Have you ever noticed how certain people seem to radiate happiness and attract others? This is because positive people attract other positive people.

In the Personal Tree of Life, you are the tree and your life is comprised of branches. Where do your branches lead you? You need to feed your tree with sunlight and water to help your branches grow because branches reach out into the unknown. By building a strong foundation of roots, you’ll be able to take on changes which help you grow and nurture yourself. Feel rooted in the decisions you make. Trust that where you are in life is where you a supposed to be.

In other words, do you feel good enough about yourself to date? This is a vital first step that requires you to be honest with yourself. Think of positive aspects in your life that you can improve; get in shape, be satisfied and happy with your career, family and friends.

In Anderson’s article he describes assessing your self worth: “People with low self-esteem tend to create relationships with others who evaluate them negatively. If you're suffering from a negative self-image, it's vital you take steps to create a positive, healthy self-concept.”

2.“I don’t know how to date.”

The first step to dating is feeling good. To help recognize your good traits, write a list of positive affirmations about yourself and keep them posted somewhere you can see them. This will help you manage self-doubt by accepting who you are today. It’s important to honor yourself in the present so you can kick start goals to get you moving - mentally and physically - in the right direction.

Motivational speaker, self-help author and life coach Tony Robbins discusses the challenge of taking negative thinking and making it useful to you:

“Decide to develop the habit of focusing on what is right in your world instead of what is wrong. Make it a habit to focus on what you do have, instead of what you don’t have in life. As basic as this is and as well as you already know it, you’ve got to start creating a habit because this habit forms the chain of your ultimate character - of who you become and how you end up living your life.”

The next time you find yourself thinking, “I don’t know how to date,” remind yourself not to let your own self-doubt and fear hold you back. Set the stage and put your life in motion.

3.“What do I do?”

This is a methodical process. Think about your comfort level and assess your fears. Don’t jump or force yourself into anything. If you are a widow or divorcee it’s important to remind yourself that you’ve already been through the hard parts of life and that you can do this.

Take active steps. You won’t find a new partner or friend by sitting around the house. Anderson advises you make a list of 20 activities you would enjoy doing with the perfect partner. This will help motivate you to be active and not feel like your whole life is on pause.

Look around at online dating websites. If you feel uncomfortable or are worried about an ex seeing you online, make the choice to start off small. You don’t have to post a profile picture. You can still interact with others and look around to get yourself familiar with online dating practices.

‘Start off small’ can also mean visiting smaller dating sites. Large communities like and eHarmony can be unnerving. Try choosing a small dating website so it’s not as intimidating and full of people. Some of these sites are better at finding you a new partner who shares your common interests or values. The Huffington Post article,  “5 Reasons to Go Niche When Looking for Love Online” by Laurie Davis, is full of practical reasons why you may want to start out in a smaller dating space. Davis suggests websites like,,, and as good sites to consider.

4. Open Your Network

Making new friends and opening your self up to new relationships can seem challenging. It is important to open up your world because you never know whom you’ll meet at any given time.


Consider hobbies you enjoy or activities your former self used to love. Maybe you played a lot of tennis in college. Get back into it! Join a tennis group or clinic.  Who knows, your next doubles partner could be the love of your life. Pursuing interests will put you back in the people arena. Making new friends and expanding your social network will give you a new support system and help grow your self-confidence.


Yolanda, from Anderson’s article, discusses the benefits of opening herself up after divorce. “My divorce split our extended families and friends," she says of her and her ex-husband. "But my new friends had a fresh perspective that helped my self-esteem. Those who were single had confidence that was contagious; that really helped me when I started going out again as a single person. And sometimes they offered good advice."

5.  Nervous about First Dates? 

Ushering in a whole new set of hang-ups, a first date can be tough. The following reading list for men and women is packed with advice on how to dress, appropriate first date topics, things to avoid saying and much more:

6.  The First Date

         You’ve jumped over the hurdle of fear & uncertainty and gotten yourself a first date! Now you need to figure out what to do and what to say. The most important thing to remember is not to overschedule yourself on the day of your date. Avoid scheduling dates right after work when you’re flustered, feel and look disheveled from the day and need to unwind. Cassie & the IM editorial team offer this set of first date guidelines before you start planning: “Your Ultimate Guide to Successful First Dates