The holidays have a way of forcing conversations you’ve been putting off.

You’ve been dating him for ten months. Things are getting serious. You’ve met his five-year-old son multiple times. But your family still doesn’t know he has a kid. And now the holidays are here, and he wants to bring his son to your family dinner.

Suddenly the “right moment” you’ve been waiting for has arrived whether you’re ready or not.

This week, a listener named Kayla reached out about this exact collision: a relationship that’s getting real, a secret that’s gotten too heavy to carry, and a holiday deadline that won’t wait.

She shared:

“I’ve been dating this guy for 10 months now and things are really getting serious between us. He has a five-year-old son from a previous relationship, and I’ve met him a few times. He’s a great kid. I really care about both of them. But here’s where I’m stuck. My family’s having their big holiday dinner, and now my boyfriend wants to come. He wants to bring his son. Part of me loves that. But I haven’t told my parents he has a kid yet. I know I should have mentioned it earlier, but it felt too soon, and now it feels too late. Do I tell them before he comes or should I tell him to come next year instead? I really feel like this guy could be the one, and I don’t wanna mess this up.”

This is a question that goes deeper than holiday logistics: Can I commit to this relationship and everything it actually includes?

(02:40) The Omission Itself Has Become the Problem

Here’s the truth sitting underneath all of this: the silence has become bigger than the secret.

When you keep something significant hidden, silence creates its own story. Your parents will wonder why you kept this from them. And the longer information sits unspoken, the more weight it takes on, even when it really shouldn’t be that big of a deal.

What you’re really carrying right now:

• The guilt of not mentioning it when it mattered
• The growing anxiety about the reveal
• The fear that naming it makes it feel more serious
• The weight of compartmentalization itself

Every day that passes, that load gets harder to carry.

(03:20) If There Were No Deadline, Would You Still Be Avoiding This?

That’s the real question.

The holidays aren’t creating the problem. They’re just creating artificial urgency around a conversation that probably should have happened months ago, back when you met his son or when it started to seem serious.

You need to separate the holiday pressure from the relationship reality. Ask yourself this: If you’re not comfortable telling your family that he has a child, why? Is it your parents’ expectations, or is it your own?

Sometimes that fairytale we’re protecting is actually the one we’ve been writing in our own heads. Maybe it includes a fear of letting him down. A fear of letting his son down. A fear of suddenly becoming a mom when that wasn’t on your life path before.

This isn’t about whether you should tell them. It’s about whether you are fully ready to commit to this relationship and everything that it includes.

(06:00) This Isn’t Halfway In Territory

Ten months in, you’re not in “let’s see how it goes” anymore.

When you are dating somebody with a child, especially a five-year-old, this means you’re accepting a possible outcome where you’re going to be in this kid’s life. For a very long time. And you likely would be part of raising this kid in some way.

That’s the really big question that has to be answered at the beginning: Am I really okay with this?

Here’s what we hear from people: 

“I don’t see myself dating someone with a kid.” 

“I don’t really wanna deal with any baby mamas.” 

But here’s the reality: Love is love. 

You can’t control what somebody’s backstory is. Your boyfriend did not intend to have a child and then have a breakup. These aren’t experiences people go out seeking. Yet they become part of our story.

When you’re in a relationship with somebody who has a more complicated story, you have to consider how to reframe your own expectations. This could be a wonderful thing he’s bringing into your life. And there may also be an adjustment period as you grapple with what is and how you wished it would be.

(09:00) First and Foremost: Do Right By the Child

There’s a child involved here, and that changes everything.

This isn’t just about your relationship with your boyfriend. It’s about a five-year-old who’s already met you multiple times and knows you exist in his life. If things are serious enough that you’re considering family holiday gatherings, they’re serious enough that this child matters.

You have a responsibility here. If you really feel like he’s the one, you want to show him that you’re accepting of all of the parts of him and his life, especially someone as important as his son.

What does doing right by that child actually look like:

• Being honest about the relationship instead of keeping him a secret
• Showing up as someone stable and present, not someone hiding
• Integrating into his life in a way that’s real, not compartmentalized
• Being willing to step into whatever role this becomes

First and foremost, you have to do right by that child. Not eventually. Now.

(10:40) The Holiday Isn’t Actually the Problem

You’re asking me if you should push this off until next year. But here’s the thing: there’s no perfect time. Actually, the holidays might not be the worst time.

Having everybody gathered and having it be a big family experience, it sort of just drops him right into the fast lane. You don’t have to go through introducing him one by one. Everybody’s here. He gets to know them in little bites, in small bursts. In a big gathering, it’s sometimes easier for him to figure out where he fits within the family order.

But you absolutely cannot show up with a surprise child at the holiday dinner. Your fear of their reaction is valid. But it’s not a reason to ambush them or keep living with a secret.

Telling your parents now, not tomorrow, not just showing up:

• Gives them time to process
• Shows them respect
• Allows them to do a rewrite of their own story

You also can’t put your boyfriend in a weird position. Where he has to ask his ex to take the kid for the holidays so he can go with you. That’s just way too complicated. And it signals to him that you’re not fully in.

(13:00) The Door Is Being Opened

If you rescind the offer to your boyfriend, the one you said could be the one, what message does that send? Does it make him feel like he’s on that trajectory with you? Or does it make him feel like he’s being put off or let down easy or hidden?

Big events can be scary. Big life transitions can be scary. Claiming someone and declaring your intent in a relationship can be a lot.

But you know the best thing to do.

There’s a moment being created for you right here. The door is being opened. You have a choice. And it may be time for you to just bravely walk through it.

The gift you give yourself and everyone else is the truth, even when it’s uncomfortable. Especially when it’s uncomfortable.

💌 Got a question about blended families, telling your family something you’ve been hiding, or conversations you’ve been avoiding?

Whether it’s about introducing a partner with a child, managing family reactions to complicated relationships, figuring out if you’re truly ready to integrate someone into your life, or just needing permission to have the hard conversation, send it our way.

DM @DamonaHoffman on Instagram, TikTok, or Facebook, or leave a voicemail or text at 424-246-6255. Your question might be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the significant relationships in your life. Your romantic partners. Your family dynamics. Your own readiness to step up. And most importantly, the courage underneath your hesitation.

📝 Want to keep track of what’s working in your dating life? Download the free Date Tracker at damonahoffman.com/datetracker