How Do You Know When You're Ready to Date Again?

After the death of a spouse, finding the interest to date again can be a challenge.

A few months after I lost my wife to cancer, a dear friend, a mentor really, approached me with some words of wisdom. His advice and counsel had been a source of encouragement to me for forty years. When he spoke, I listened. So, when he called to check on me, tell me he was praying for me and looked forward to our next time of fellowship, he closed by offering a few words of warning. 

“Look out for the casserole ladies!”

Say what? He chuckled as he went on to explain that I should not be surprised if ladies from my parish started showing up at my front door with casseroles. While their compassion would be admirable, they might have other motives in mind.

I laughed—until the doorbell started ringing.

I turned 60 just three weeks after I lost my wife. Given my age, balding head, and a few excess pounds, I hardly expected any woman to be interested. Besides, after a 38-year, deeply satisfying marriage, I had no interest in dating again, much less marriage. But, three years later, when my grief had softened, I found myself contemplating asking someone out on a date...

And, it was a scary thought!

How did I know I was ready to date again? 

There is no magic number or exact formula for when you should consider dating again. I know many widowed spouses who have zero interest in dating, wanting instead to savor the memories of a decades-old marriage. Still, others, are too frightened or have such low self-esteem, that dating is not worth the disappointment or risk of rejection.

So, how did I know I was ready to re-enter the dating waters? Here are six things to consider—you might be ready to date again when:

You have allowed yourself time to grieve.

Ecclesiastes speaks of a time to mourn. By implication, that “time” is not forever. Yes, grief may always be a part of your life. Why wouldn’t it be? But it doesn’t have to be a never-ending, overwhelming, heart-rendering gut-punch to your soul. Life goes on, your spouse would want you to move on, and the Lord is certainly not finished with you yet. 

I knew a man who remarried six months after the loss of his wife. I wondered if he had time to process his grief. Or was he too focused on finding a “replacement” spouse? Everyone grieves differently, but allow yourself time to grieve so that your emotions will not be conflicted if and when you do date again.

You have your priorities right.

I resolved during my grief period that I did not have to be married (again) to be content. My faith sustained me, and my focus was on following Christ. I wasn’t on a hunt for a new bride. Ironically, that perspective freed me to accept whatever path the Lord had me walk. I found myself equally open to either celibacy as a senior or remarriage. For me, recognizing I did not have to date or marry to be content also served as a green light that it was ok to date again.

Matthew Kelly in his book, The Rhythms of Life, declares that we can never get enough of what we don’t really need. Rather, he argues, we need to focus on discovering our deepest desires—those things that will help us become the best version of ourselves. My priority was/is my faith in Christ. Yet, I knew that God had used my marriage to help me grow as a man, a husband, a father, and a man of faith. I found meaning and purpose in my faith. The question I had to answer was—would a second marriage serve that same purpose?

You have evaluated your motives.

Why do you want to date? Are you open to being married again? Is it just for companionship? Sex? Soon after joining CatholicMatch, I met a lady who seemed preoccupied with sex. She made it clear to me that sex was important to her. So much so that her focus on the physical highlighted her less-than-impressive focus on the spiritual. It was a turnoff. If you decide to date again, do so for righteous reasons. To be clear, sex should not be your number one reason to date again.

You sense that the excitement has returned.

When I started dating again, my emotional response seemed eerily like that of my teenage dating years—butterflies in the stomach, second-guessing where to take her to dinner, a heightened awareness of my appearance. When/if I should kiss her goodnight. I was nervous and excited. These are good signs—signs that, yes, maybe you are ready to date again.

You don’t compare your dates to your late spouse.

You are ready to date again when you enjoy dating someone for who they are and not for how they resemble your late wife—either in looks or personality. If I learned anything during my time on CatholicMatch, it was how unique every woman is. Yes, we are all made in God’s image, but each of us reflects different qualities. Respect and engage your date for who she is!

You no longer feel guilty about dating.

So many widowed spouses think they are betraying their late spouse if they start dating again. I was faithful until death did us part. But, sadly, death did separate us. While I will never judge someone who finds it impossible to be open to a new relationship after a long, successful marriage, neither will I judge someone for being open to a new one. The focus, as noted earlier, should be on following the Lord. And if He leads you into a new relationship, be open to it. It may only be one of friendship, but it might also be a romantic one with marriage as the outcome.

Let your heart be your guide.

My friend’s advice about watching out for the casserole ladies may have some basis in truth, but I suggest to those recently widowed to be careful not to isolate themselves. After a spousal loss, it is normal for the surviving spouse to need some time alone, to cry, grieve, and savor the memories. I, too, grew weary of so many folks asking me, “How are you doing?” I knew such inquiries were made out of love and concern, so I was always grateful for their concern. But rarely did I confess how I was really doing. 

There is no magic number of months to grieve, but I suggest that if, after a year, your grief is still raw and impacting how you spend your time outside the home, you may need to seek counseling. 

If dating is too daunting for you, be honest with your “date” and confess your desire to focus on friendship first and enjoy the companionship of a new friend. That’s ok. There’s nothing wrong with falling into “Like.” Who knows, it may lead to falling into love.

In the meantime, never turn down any casseroles. They are usually quite delicious.