Are You Ready To Date Again?

Gearing up for a return to romance after divorce or widowhood? Let these 8 guidelines be your back-in-the-saddle barometers.

By Chelsea Kaplan

hether you’ve endured a divorce or the loss of a spouse, deciding on the right time to begin dating again can be difficult. Often it’s emotional baggage that’s keeping you from jumping back into the dating pool, but reasons like lack of confidence and feelings of guilt can also serve as roadblocks on the path to finding new love. How do you choose the right time to take another shot at finding The One? Below, Carole Brody Fleet, author of Widows Wear Stilettos..., offers her tips on when you can best gauge the right time to begin dating again.

1. When you have recovered from your grief
“Immediately following divorce or death, at the height of grief or during what may very
“Trust yourself that you’ll know when the time is right.”
well be the worst time in your life is not the time to jump headlong back into dating,” Fleet says. Like it or not, before resuming dating, you must first heal from the pain of the divorce or death of your spouse. Unfortunately, such recovery doesn’t occur overnight. “Before dating again, take the time and patience to sufficiently recover from the trauma that you have experienced and to get to know yourself as a single person,” Fleet recommends. Don’t let other people’s urgings that it’s time to get back out there again sway you. Trust yourself that you’ll know when the time is right.

2. When you realize that you are not guilty
When you have been functioning in life as one-half of a couple, you become conditioned to thinking of yourself in those terms, Fleet says. “It’s jarring when all of sudden — whether by divorce or by death — you are single, yet your emotional being is still in the ‘one-half of a couple’ mindset,” she explains. When you find yourself attracted to someone or you make a decision to resume dating, you may feel guilty, almost as if you are cheating on your ex or late spouse, not to mention your children, his family or all of the above.

While guilt is a perfectly normal emotion to encounter during healing process, it can nonetheless hold you back from returning to dating. “You’re realizing and accepting that your previous relationship has ended and that there is no reason to feel guilty about dating or seeking companionship is a necessary step in the knowledge that you are ready to re-enter the world of dating,” Fleet says.

3. When you’ve let go of your anger
It is absolutely normal to feel angry at whatever circumstances ended your relationship. “Of course you’re going to be angry with an abusive or unfaithful spouse or at the circumstances surrounding a spouse’s death—after all, you’re a good person and you did not deserve this,” Fleet says. Sadly however, Fleet says many choose to stay “in the angry” or “in the bitter” to the point that they are unable to move forward with their lives. “These same people may take this anger out on their children, their friends, their work colleagues and yes, prospective dates as well,” she notes.

The resolution of your anger is an important step toward readying yourself for dating again. “When you have made peace with the circumstances that ended your last relationship and you have begun to move forward from that loss into your new life, you are truly ready to begin exploring the world of dating again,” Fleet says.

4. When you’ve left the “ghost of marriage past” in the past
Fleet points out that many people who are widowed or divorced have “selective amnesia” when it comes to their previous relationship: remembering only the good in the person no longer in their lives, the good times that they had with them and the good memories that they’ll have always. Sometimes, the case is just the opposite, and only bad memories remain. “Avoid using your previous relationship as a ‘yardstick’ against which you are measuring prospective dates—they will not be able to compete,” Fleet cautions. “By all means, treasure the wonderful memories that you have and try as best as you can to let go of the painful ones, but before you begin dating again, you must put the ghost of relationships past in its proper place in order to enjoy someone new.”

5. When you’re happy being on your own
Are you content within yourself as a single person, on your own without the necessity of the presence
Work towards being able to go out alone and enjoy your own company.
of another person? Being happy by yourself means a contentment to be in your home by yourself—with or without children, and that you have a life that is your own and is fulfilling in its own right, Fleet notes. “Do you have your own career, your own hobbies, your own pursuits, your own set of friends with whom you play sports, lunch, drink or dine?” Fleet asks. “When you are content with yourself, you are genuinely ready to begin the dating process again, because you are not simply filling the void that your last partner left behind; you are instead opening your heart and your mind to the possibility of a new relationship.”

6. When you can go out alone and have fun
The “companion” element to being happy on your own is the ability to go out alone and enjoy yourself. Fleet says, “As a society, we are accustomed to either traveling in packs or with a spouse or significant other; however, you must be happy and content with your own company both within your four walls, as well as in the outside world before you should begin dating again.” To get to this point of self-sufficiency, Fleet suggests going out to dinner or to a movie by yourself. “Finding this contentment will enable you to make wise decisions in your dating choices and when you do meet that someone special, it will be for all of the right reasons,” she says.

7. When you’re truly emotionally available
According to Fleet, your emotional availability will have everything to do with not only the amount of time that you have spent recovering from your divorce or the death of your spouse, but also your willingness to make yourself emotionally available. “I once dated a man who had not recovered from being broken up with in high school—thirty years earlier!” she remembers. “This gentleman made a conscious decision not to make himself emotionally available to anyone else because of a prior bad experience.” Her advice: Ask yourself if you are truly ready for the dating experience and if you are capable of making yourself emotionally available to another. “If you don’t feel quite ready yet, back up and take more time for you, but please don’t take thirty years!” she advises.

8. When you’re capable of trusting again
Nearly everyone has been taken advantage of and otherwise treated shabbily by a former mate. Should we learn from our past experiences in order to avoid repeating history? Definitely. Should we take our past out on our future? Absolutely not, says Fleet: “To make the unilateral decision that ‘All men lie and cheat’ or ‘All women are gold-digging opportunists’ rather unfairly condemns an entire sex because of the actions of a few.” Regardless of your history, you must have the ability to trust others before you begin dating again. If you judge others on the misdeeds and wrongdoings of the last person in your life, Fleet says you’ll be doomed for disappointment on the dating front.

Put all this advice together, and here’s the bottom line: The whole process of re-entering the dating world after divorce or death is rather like testing a bruise to see if it still hurts. Fleet says: “Have you ever had a really nasty, awful-looking bruise? After time, it may look like the bruise is all cleared up, yet when you push on the spot, it still smarts a bit. By the same token, there is a bruise of sorts on your heart as you recover from the loss of your spouse; whether by divorce or by death.” As with a bruise, Fleet advises that from time to time, you push on that spot in your heart. “If it’s still too painful… quit pushing—it means that it’s not time for you to be dating yet!” she says. However, eventually that tender spot in your heart does heal—and so will you. “You will know when the time is right if you listen to and trust in yourself,” she asserts.

Chelsea Kaplan is deputy editor at Her blog, “I’m Somebody’s Mother?” can be found at
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