Is It Too Soon After My Cancelled Engagement to Start a New Relationship?

Hey, Best Friend!

I just got out of a 3 year engagement, and immediately started dating a coworker of mine. I really like him, but I'm not sure if it's too soon. He's about 10 years older than me and everything my fiancé wasn't. Should I keep it going or take a seat?

Hi Bestie,

Why the three year engagement? 

There are many reasons why an engagement could’ve lasted that long, but I feel it’s because you both knew something wasn’t quite right. So, you do the responsible thing and cancel your engagement. But, then start dating your coworker?! Ma’am! 

You stated that your coworker is not only significantly older than you, but he’s “everything your fiancé wasn’t.” It sounds like you are trying to run away from the things you think may have contributed to your engagement ending.

Best friend, that can have detrimental consequences.  I think you need to take a break and just reset. Reset mentally, emotionally, and physically.  I suggest you take a seat and enjoy getting to know the new, single you.

Love you, Best Friend!

Now, for some "professional" advice (wink).

Life doesn’t always go as planned. Sometimes, what was supposed to be a walk down the aisle ends in a painful, unexpected cancellation of an engagement. If you’ve been through this, first—take a deep breath. You’re not alone. Many people have stood where you’re standing right now, feeling torn between healing from heartbreak and wondering if it’s okay to open your heart again.

So the question comes naturally: Is it too soon after my cancelled engagement to start a new relationship?

The truth? There’s no one-size-fits-all answer. But there are thoughtful ways to reflect on where you are emotionally and whether stepping into something new is right for you right now.

1. Acknowledge the Grief Before the Glow-Up

Ending an engagement—whether you called it off or your partner did—can feel like a loss. Not just of the person, but of the future you imagined: the wedding, the home, the family milestones. It’s natural to grieve what could have been.

Ask yourself:

• Have I allowed myself to process what happened?

• Am I avoiding my feelings by jumping into someone new?

Sometimes, a new relationship can serve as a distraction instead of a healthy new chapter. Make sure you’re not using someone else’s affection to patch over wounds you haven’t tended to yet.

2. Redefine What Healing Looks Like for You

Healing doesn’t look the same for everyone. Some people need months—or years—before they feel ready to date again. Others may feel clarity and peace surprisingly quickly.

Signs you might be moving in a healthy direction:

• You can think about your ex without overwhelming anger or sadness.

• You’ve reclaimed parts of your identity outside the relationship.

• You’re curious about love again—not desperate for it.

If you’re still replaying old arguments in your head or feeling haunted by “what ifs,” you may need more time before diving into something serious.

3. Evaluate Your Readiness Honestly

Instead of asking, Is it too soon? try asking:

• Am I ready to be present for someone new?

• Can I communicate my needs clearly without dragging past pain into it?

• Do I truly want a relationship, or am I craving comfort and validation?

If you find that your answers lean toward seeking validation or filling a void, it might be wise to pause. If, however, you feel genuinely open to building something authentic—without comparisons or unresolved baggage—you may be more ready than you think.

4. Don’t Fear Starting Small

A “new relationship” doesn’t have to mean a rush back into commitment. It can mean exploring companionship, practicing vulnerability, and easing into trust again.

It’s okay to:

• Date casually with honesty about where you’re at.

• Set boundaries around emotional availability.

• Move slower than you did before.

Not every coffee date has to lead to forever. Sometimes, simply allowing yourself to connect again can be a powerful step toward rebuilding trust in love.

5. Remember: Timing Isn’t a Rulebook

Society loves timelines: how long to wait before dating, how soon to move in, how many months before marriage. But the truth is, healing and readiness aren’t bound to a calendar.

Some people will tell you, “It’s too soon.” Others will cheer you on. But only you know when your heart feels both tender and open. Trust your own pace—not anyone else’s.

Whether you wait six months, a year, or just a few weeks, the most important thing is how you approach a new relationship. If you walk into it with honesty, self-awareness, and the courage to be vulnerable, it can be a beautiful new chapter—not a rebound.

So, is it too soon? Only you can truly answer that. But know this: a cancelled engagement doesn’t cancel your right to love, joy, and partnership. When you’re ready, love will meet you right where you are.

Your turn, Best Friend: How did you know you were ready to date again after ending a relationship? Share your story—it might just be what someone else needs to hear.