Dipping Your Toes into Dating: How and When to Start

This is my year for deepening connections—within my friendships, my professional world, and yes, I’m stepping back into the dating world.

As widows, connection takes on a new meaning after loss. At first, it’s about survival, about steadying ourselves in the wake of the unimaginable. We build a life we never expected to live, and in the process, we learn how to stand on our own. Over time, though, something shifts. We start to recognize gaps in our support system. We realize we miss certain kinds of connection—the spontaneous coffee dates, the easy companionship, the laughter that comes when someone just gets you.

For some of us, that gap also includes romantic love. I know it does for me.

It has been ten years since Steve died, and I have dated in the past. I was in a two-year relationship that ended because he wasn’t my forever person. And yet, the experience taught me that I do want partnership. I want someone to share my life with—someone to travel with, to talk through the little details of the day with, to experience life’s joys and challenges with. And so, with a mix of excitement and trepidation, I am stepping back into the dating world.

When Do You Know You’re Ready to Date?

There’s no universal timeline for when a widow “should” start dating again. Some feel ready after a year. Others wait a decade or more. Some never feel the need to seek a new relationship, and that choice is just as valid. There is no right or wrong time—only the time that feels right for you.

But how do you know if you’re ready? Here are a few signs:

• You enjoy your own company. If you can sit with yourself—your thoughts, your feelings, your memories—and still feel whole, that’s a sign you’re in a good place emotionally.
• The idea of dating feels exciting (even if it’s also terrifying). It’s natural to feel nervous, but if part of you is curious, that’s a green light.
• You’ve made peace with your past love. This doesn’t mean “moving on” or forgetting. It means carrying your past love with you while making space for something new.
• You’re willing to embrace uncertainty. Dating is unpredictable. You may meet wonderful people, and you may have moments of frustration. If you’re ready to take it as it comes, you’re ready to try.
• You want a partner, not a replacement. A new relationship will be different from the one you lost. If you’re looking for a new kind of connection, rather than an attempt to recreate what you had, you’re on the right track.

If you nodded along to these, it may be time to dip your toes into dating.

How to Start Without Feeling Overwhelmed

Dating again means stepping outside your comfort zone. It requires vulnerability, courage and a willingness to embrace the unknown. That can feel daunting—but the good news is, you don’t have to go from zero to a committed relationship overnight. You can ease into it.

1. Start with Social Circles

Rather than jumping straight into the world of dating apps or blind dates, I’m starting with singles social clubs. I love the idea of meeting people in a natural, pressure-free way while engaging in fun activities.

These groups exist in many cities and provide opportunities to meet both men and women in casual settings. Some groups I’ve explored include:

• Base (available in major cities)
• Throwback Dating (Chicago)
• Parlor Social (NYC)

The beauty of these groups is that they aren’t just about dating. They’re about connection. Even if I don’t meet a romantic partner, I might meet new friends—people to have dinner with, to go on outings with, to expand my circle. Because the truth is, connection is the goal, whether it’s friendship or something more.

2. Get Comfortable with Putting Yourself Out There

After loss, it’s easy to shrink our world down to what feels safe. It’s easy to talk ourselves out of things—to convince ourselves that we’re fine as we are. And maybe we are. But part of thriving after widowhood is allowing ourselves to want again—to want companionship, laughter, adventure and love.

That means pushing past fear. It means saying yes to opportunities, even when we feel uncertain. It means allowing ourselves to be seen.

Here are a few gentle ways to do that:

• Say yes to invitations, even when you’re tempted to stay home.
• Try activities where you’ll naturally meet people—hiking groups, book clubs, travel groups.
• Consider a dating app (only if it feels right for you—there’s no one-size-fits-all approach).
• Be open to conversations with strangers—it doesn’t have to be a date to be a meaningful interaction.

3. Redefine What Success Looks Like

Dating after widowhood is different. You’re not dating because you feel incomplete—you’re dating because you want to share your completeness with someone else.

And that means redefining what “success” looks like. A date that doesn’t lead to a relationship isn’t a failure—it’s practice. A conversation that doesn’t turn into romance is still valuable. Every interaction teaches us something, and every experience brings us closer to the right person.

If You’re Not Ready to Date, That’s Okay Too

Not every widow wants to date, and that choice is just as valid. Some women find fulfillment through friendships, family or personal growth, and that’s a beautiful path, too.

For me, part of my journey this year is also about rebuilding my local connections. Many of my close friends have moved away, and I no longer have that one person I can call on a whim for coffee or a walk. I want to change that. Because whether or not I find a romantic partner, I know that friendship and community are essential for a full life.

If you’re not ready to date, ask yourself: How can I create more connection in my life?

Maybe it’s joining a new group. Maybe it’s reconnecting with an old friend. Maybe it’s simply opening yourself up to new experiences, knowing that love—in all its forms—finds us when we’re open to it.?

Final Thoughts: Take the Leap

Dating again isn’t about replacing the love we lost. It’s about expanding our hearts to new possibilities. It’s about creating space for joy, companionship and maybe even a second great love.

So, if you’re feeling the nudge, take the leap. Say yes to an invitation. Join a social group. Allow yourself to imagine the possibility of love again. You never know what beautiful surprises are waiting just outside your comfort zone.

And I would love to hear from you. Have you thought about dating again? What has your experience been like? What has helped you feel ready—or made you decide that dating isn’t for you?

Wherever you are on this journey, know that you are not alone. I am here to support you, to listen and to cheer you on every step of the way. ??