For some people, the answer is never.
They have no intention of seeking a new life partner; they want to cherish the memory of their late spouse, and marrying, much less dating, someone else feels like they are cheating. I respect that view, though I disagree with its assumptions.
For others, dating again feels too intimidating. Their last experience was probably many years ago in high school or college. Dating customs have evolved several times, making 21st-century dating feel like a completely different world.
When I started dating back in 2016, it dawned on me that the last time I’d kissed someone other than my (late) wife, Lyndon Johnson was President. Forget romance, the thought of kissing someone else scared the dating idea right out of me.
So, how do you know when it’s time to start dating again?
There is no easy answer. Because the answer is different for everyone, we all grieve differently and must allow the grief process to run its course. The Bible says there is a time to grieve, implying that it is not something you do forever. Reality suggests that for most of us, losing a spouse in a long and successful marriage will leave us grieving forever. Oh, the raw, punch in the gut, cry in a corner kind of grief will slowly fade into a dulled and loving ache whose painful feelings become intertwined with loving memories.
During my grief process, I developed a profound sense of gratitude. I started to thank God for the blessing of a loving wife, the 38 years we shared, and the man I became because of her loving encouragement and support. It was her encouragement that, after a few years, opened my heart to the possibility of finding love again. My three daughters also gave me permission to “get out there.” "Dad,” they said, “you are a nice guy and there are not enough nice guys out there.”
For me, I had my “time to grieve." I also experienced a period where I lived a single, celibate lifestyle filled with meaning and purpose. I was content and understood that I didn't need to be married to have a fulfilling retirement. To my surprise, this attitude gave me the freedom to be open to dating.
Over the past fourteen years, I have talked with many widows and widowers about this question. Their answers varied but shared a common theme:
- There is no set timeline. Someone else’s experience (good or bad) doesn’t mean you have to follow in their footsteps.
- The decision to date is personal. Others may advise, encourage, or even berate you for not jumping into the dating pool. It is up to you to prayerfully consider your life and when, if ever, to be open to the possibility of a new relationship.
- Not to be redundant, but take your time. Focus on healing and allowing the grief process to run its course; for most folks, that’s about a year, but not likely more than two.
- Don’t allow the dating option to serve as a distraction from grief. That’s a bad motive and one that likely will have negative consequences.
- When the right person comes along, stepping off the grief train is easier than you might expect.
One way you might realize it’s time to move on is when you reach the point of genuinely loving a new person in your life.
This doesn't mean you stop loving your late spouse; instead, you can now give your new partner your full thoughts and attention. No one wants to compete with a memory, so you must recognize when you've reached that point where you can focus on a relationship in the present without the cherished memories of the past acting as a lingering distraction.
I cherish the memories of my late wife and the life we shared and created. One way to handle these memories without affecting the present is to imagine them as a photo album on a shelf. Whenever I want to enjoy a memory of her, I mentally remove the album from the shelf and rejoice in the blessings of the past. When I’m finished, I place the mental album back on the shelf. It’s always there, but I don’t obsess over it, nor is it a daily focus. I now have a new, wonderful marriage, so I stay focused on that.
I once heard a counselor answer this question: “You should start dating again whenever you feel like it.” Be cautious with that piece of advice. Feelings might change, but the suggestion is that deep inside your heart, you will inevitably know when it’s time to start dating again.
Be aware of your feelings.
Don’t let others pressure you. If you feel like you're being pushed into an untimely date, it's probably best to step back. Likewise, if you have within you a sense of urgency or internal pressure to jump into the dating world, be cautious and consider seeking out a counselor to help you understand your feelings.
In summary, only you know if and when you are ready to date again. When that time comes, take a moment to evaluate the areas of life you engage with. Are there co-workers, people at church, or members of your social clubs who pique your interest? And don’t dismiss the idea of online dating. At one point, I swore I would never turn to online dating. But as a Catholic seeking to date only Catholic women, I soon realized that CatholicMatch was the best option for meeting women who share my faith.
I often describe the start of my online dating journey as dipping my pinkie toe into the dating waters to see how it feels. One benefit of using a site like CatholicMatch is that you can go at your own pace. You can begin by chatting with people through email. You decide when to move on to phone calls or an initial meet-and-greet date. At any point, you can pause the process.
If something doesn’t feel right or raises a red flag, pay attention instead of ignoring it.
But, despite what others say, online dating can be enjoyable. Understand that it’s normal to feel nervous or awkward at first, but if you can relax, you might find dating to be fun.
I know. I speak from experience. To my delightful surprise, I met many wonderful women online, and one I eventually decided to marry! I would never have found her if I hadn’t been willing to explore the online dating world known as CatholicMatch.








