Dear Rachel: Ask your parenting questions now

A single dad has revealed the awkward conversation he faces with his teen daughter.

Deciding when to allow your teen to go on dates can be difficult.

An anxious mum reveals she is quietly freaking out about her son going out on his first date, while a dad is nervous about taking his daughter to the shops to buy her first bra. Parenting expert Rachel Schofield weighs in.

DEAR RACHEL

My son is going on his first date. I’m one of those mums who worries about everything, and now I’m freaking out a bit. He’s only 14, and I’m not sure how to handle this whole dating thing. How do I make sure he’s ready without coming off too overbearing, but also not letting him go out there unprepared?

RACHEL’S RESPONSE

It’s completely understandable to feel a bit flustered when your son starts dating – it’s a big step! And that’s the sweet spot – wanting to prepare him without smothering him. You’re absolutely right to pay attention to your own tendency to worry – this is key as you both navigate this new life stage. Your anxiety will be focused on your son. A good counter to this is to shift your attention inward. How can you stay reasonably relaxed and confident? That your son has everything it takes to date well.

Maybe take a calming walk, a chat with a friend, or some slow deep breathing to help anchor you before engaging with your son. After all, this is his journey. He needs space to figure things out, make his own choices (and maybe even a few mistakes along the way). Let him know you’re there for him, no matter what, but try to do so from a place of calm support rather than anxious concern. If you try to have those conversations while feeling tense, it’ll likely create awkwardness for both of you. Instead, if you can bring gentle humour and a relaxed tone to the table, it’ll make a world of difference.

There's a fine line between being overbearing and being overprotective.

Now, about those conversations …

It’s all about creating a safe space where he feels comfortable opening up. Try casually weaving in topics like respect, boundaries, and what makes a healthy relationship. It’s also important to talk about consent and how to recognise potentially uncomfortable or unsafe situations. He needs to know that he can always come to you, or another trusted adult, if anything happens that makes him feel uneasy. This builds trust and shows him he can come to you without judgment. A good dose of humour can work wonders here. Think back to your own dating escapades – those awkward encounters, the fumbled first kisses, maybe even a disastrous date. Sharing those stories, with a lighthearted touch, can really break the ice and show him you get it. Plus, it’ll probably make him feel a lot better about any jitters he’s having.

I know it can feel a little awkward to talk about dating with your son, especially at this age. It’s okay to acknowledge that with him – it might even make him feel more comfortable! Just remember to keep the lines of communication open. Check in with him from time to time (without overdoing it), not just about this first date, but about future experiences as well.

And don’t forget the practical stuff. First dates can be nerve-racking, so remind him it’s okay to feel a bit awkward. Help him brainstorm some fun, age-appropriate ideas, maybe even share some of your own from back in the day. A gentle nudge on basic manners – being on time, ditching the phone, actually listening to his date – wouldn’t hurt either.

Ultimately, who better to guide him through the ups and downs of dating than someone who’s been there, done that, and has come out the other side wiser?

DEAR RACHEL

My daughter needs her first bra and I thought I still had a while before I had to deal with this. I’m in my 40s, single dad, and I’ve got no clue how to handle this. She just brought it up, and I’m thinking, “Alright, now what?” How do I help her get what she needs without making it awkward or looking like I’m totally out of my depth?

RACHEL’S RESPONSE

It’s perfectly normal to feel a bit overwhelmed when your daughter first needs a bra. You’re navigating new territory, and you want to do right by her. The good news is that with a little sensitivity and support, you can help her through this milestone. Many parents find themselves a bit taken aback these days, as girls are hitting puberty younger than they used to. You’re not alone feeling like you’re on the back foot!

Sometimes, for single dads, it can be helpful to enlist the help of a trusted female friend, relative, or even a store associate in the lingerie section. They might even be willing to accompany you and your daughter on a shopping trip. Online resources can also provide helpful information on bra fitting and selection for young girls. When you’re looking at bras, remember that there are lots of options out there. Besides traditional bras, there are also sports bras and camisoles, which might be more comfortable for her, especially at first.

It's important to make sure teenagers feel as if they are listened to when discussing controversial topics.

When you do talk about it, frame the experience as a practical one. How bras offer comfort and support and avoid talking about appearances. Be matter of fact, in the same tone you would approach buying a new pair of shoes. Of course you may also feel awkward, it’s okay to acknowledge that! You might say something like, “This is new for both of us, and it’s okay to feel a little weird about it.” A bit of humour can go a long way in easing any tension.

Some parents like to make it a rite of passage. This could be a lovely way to mark this milestone. Perhaps you could have a small celebration, a special outing with just the two of you, or simply a heartfelt conversation about growing up. It’s a chance to acknowledge this new stage of her life and let her know you’re there for her.

Remember that the more you treat this as a normal part of growing up, the less awkward it will be for both of you. Let your daughter know she can always come to you with any questions or concerns she has about her body and development. Your support will mean the world to her as she navigates these changes.

Parenting expert Rachel Schofield. Picture: Supplied

Rachel Schofield, a leading parenting expert with 17 years experience, helps families ditch bribes and yelling for calmer, happier homes. With warmth and understanding, she guides parents to raise connected, resilient children using evidence-based strategies. Rachel’s a Professional Member of the Australian Association of Family Therapists and mum of two teenagers. Download her free guide, “How to Stop Losing It With Your Kids” and smooth out those parenting challenges.

Originally published as Dear Rachel: Ask your parenting questions now