My brother has been dating a woman for three years. My sister and I both love her and have become good friends with her. She’s included in all family activities, get-togethers, celebrations and even vacations. We’re all in our late 20s, and my sister and I love having her around.

Recently, our brother has been unhappy and moody, and we couldn’t figure out why. We’ve all been living at home together, post-university, but he and she have started looking for their own place together. We’re so excited for them!

Last week, we finally got it out of him what the problem is: they’re breaking up! And now my sister and I don’t know what to do! We have tickets to a concert with her later this month; and we’re all going camping, girls only, with some other friends for the August long weekend.

How do we remain friends with this woman while still maintaining our loyalty to our brother? Can you help us navigate this?

Sister Friends

So much depends on why they’re breaking up and how amicable their decision is/was. If she dumped him and he’s devastated, you may have to take a break from the friendship while you help him heal his broken heart. If he dumped her because of bad behaviour on her part, you may want to rethink your friendship anyway.

But if he broke up with her simply because the relationship had run its course, you and your sister would need to talk to him, and hopefully, he could be generous and allow you to help her through this rough time.

At the end of the day, he’s your brother and your loyalty must be to him first and foremost, especially based on your close sibling relationship.

My boyfriend is the nicest guy. He’s got a good job, dresses nicely, is respectful of me and always wants to have a good time. We’ve been together six months and I really like him. My issue is that I don’t see any motivation from him to advance, in both his life and his career. He’s just content with his life as is.

I guess there’s something to be said about that, but at our age, we’re both 27, I feel he’s wallowing in complacency and it’s upsetting to me. If I’m really honest, I don’t find it an attractive trait.

How do I talk to him about this? I fear it will impact on our future.

More to Life

From the way you’re speaking, I get the strong impression that you and your boyfriend are simply at different stages in your life, even though you’re the same age. At 27, he’s not feeling pressured to succeed any more than he already has. You didn’t mention, but perhaps he comes from a wealthy family where financial success isn’t a goal or a motivating factor.

He’s content living his life in the manner at which he’s doing so right now. Might he change? Maybe, but you sound as though you don’t want to wait around to find out. You don’t have to. There are plenty of nice guys out there who dress nicely and will show you respect.

But before you walk away, have you attempted to discuss this with him? If no, then he’s not getting a fair shake. Tell him what’s bothering you, what’s planting doubt in your heart about this relationship. Listen to his response. Then make your decision.

If you’ve already had this chat with him and he’s expressed that this is who he is and what you get, you need to accept that he’s not who you want to spend your life with. Move on before you get any closer.

FEEDBACK Regarding caring aunt (May 19):

Reader – “This young man may not be fully ready for a relationship yet. Maybe he’s already dating, but not ready to introduce anyone to the family. Not everyone pursues relationships at 22. Some wait, pursue other life goals, then seek this. Those who are pushed into relationships early often don't fare well. Let this be his decision, when he’s ready, whether now or later.”

FEEDBACK Regarding Daddy’s little girl (May 20):
Reader – “I grew up a Daddy’s Girl, and my mother was a strict disciplinarian. Although it’s important for parents to be on the same page, in my home, whenever I asked my dad for anything, his response was, ‘I’m OK with it, as long as your mother agrees.’

“This prevented me from manipulating and playing one parent against the other. It stood me well in raising my own daughters.”