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Single and Dating. . . Again!

In the immortal words of Neil Sedaka, “breaking up is hard to do.” But it isn’t the hardest thing to do. Finding yourself newly single after an extended romantic relationship and facing that awful question of what to do on Saturday night is much harder. How do you get over your old relationship while, at the same time, opening yourself to new possibilities? How can you cope with feelings of insecurity and uncertainty as you once more step cautiously into the dating scene? Who will you meet, and where will your next relationship take you?

First Things First: Working Through the Loss

The feelings of loss that accompany the ending of a dating relationship are common and need not be feared. It’s your mind’s way of letting you know how close that person was to you and reminding you that life is challenging and often unpredictable. Losing a significant relationship in your life is not much different from losing a person to death.

There are five stages of grief that many people go through as they learn to accept the loss. Elisabeth Kubler-Ross has categorized and described these stages through decades of research. The stages include denial, anger or resentment, bargaining, depression, and finally, acceptance. Many people will recognize these stages in themselves, and in other situations that involve a loss. It is generally considered healthy for a person to go through these stages to arrive at a place, emotionally, where they can begin to carry on with life.

It is, in some ways, more difficult to recover from the loss of a close relationship when that person is not only alive, but dating others. The intensity of the loss can be multiplied when our imaginations are allowed to run wild with thoughts of the other person in a new relationship while we feel stuck in a stage of doubt and self-pity.

The loss of a relationship must be fully appreciated and the mix of feelings that loss evokes must be experienced before you can move on. Until you are able to let go of a relationship that has ended, it will be difficult to open up your life to another individual. Allow yourself the time and emotional energy it takes to work through your feelings of loss before moving on.

Making Better Choices in the Future

We can learn a lot from old relationships if we only take the time to sit down and try to figure out what went wrong. Too often, people are in such a hurry to put the old relationship behind them that they spend no time in trying to examine what was good and what was lacking in that relationship. Examining and learning from a relationship is not the same as analyzing it to the point of obsession; spending some quiet, reflective time, writing in a journal, talking with a friend, or talking with a professional can help you put a relationship that has ended into perspective and assist you in moving on.

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One way this learning process immediately benefits you is that it can help improve your self-esteem and outlook. Try to be honest about what happened in your last relationship: it’s rarely the case that one partner can be faulted for a relationship that didn’t succeed. Each person brought something to the table, but it didn’t work out as you had hoped it would. Sometimes it’s a matter of two people simply not being as compatible as they thought they were (a fact often discovered only after marriage or moving in together). Sometimes it’s a matter of not knowing the other person well enough, or the relationship being one-sided in terms of emotional or daily support.

By determining what was right with the relationship, as well as what was wrong with it, you can be in the position of making better judgments about future involvements. Remember, nothing in life is simply black or white. Relationships, as much as anything else in this world, are composed of fine and varying degrees of gray. Learn to discern those grays and you’ll be well on your way to having healthier, happier relationships in the future.

“Breaking In” a New Relationship

One difficult aspect of leaving a familiar relationship is the tendency to compare every new dating partner to your old flame. It may help to know that, at first, nobody will be able to match up to your lost love. You’ll miss the comfort of being with someone who knew you so well that, on some occasions, words just weren’t necessary. Being with someone new can feel strange and unfamiliar, and will likely require you to “teach” this person about the way you think and feel (and vice versa).

Slowly, this period of awkwardness passes, and you come to realize that the other person has many attributes that you find endearing. The other person is also learning about you, and coming to know your strengths and weaknesses as a potential partner. The more compatible the match, the more likely it is that you both will value those attributes you each bring into the relationship.

Two people who share common values and at least some common interests usually will get along easily and well over time. The hardest part is sticking it out long enough to move past the obstacles that inevitably arise in the “getting to know you” process. Remember that it will take time to build the kind of familiarity and comfort you came to experience in your previous relationship, but it can happen once again and may well be worth the effort.

Single and Dating. . . Again!

Robert Stone

APA Reference
Stone, R. (2020). Single and Dating. . . Again!. Psych Central. Retrieved on September 27, 2020, from
Scientifically Reviewed
Last updated: 17 Jan 2020 (Originally: 17 May 2016)
Last reviewed: By a member of our scientific advisory board on 17 Jan 2020
Published on Psych All rights reserved.