DEAR NATALIE: My brother wanted to propose to his girlfriend last month but didn’t have a lot of money for a ring. I had broken off my engagement earlier in the year because I caught my fiancé cheating – he felt bad about all of it and let me keep the ring. It was valued at $7,500 when my ex bought it. I told my brother he could buy the ring from me for $3,000, and he agreed. My older sister and her husband witnessed this arrangement while we were at my house having dinner. So, he proposed. She said yes and she went to have the ring appraised. They appraised it at $5,000. Now my brother said he won’t give me what I asked and what he agreed on. He wants to give me $2,000, instead. His fiancee doesn’t know about how he re-used my engagement ring. (She never saw it when I was engaged). I don’t know what to do because this isn’t what we agreed on. I told him if he won’t give me the amount that we agreed on, he needs to give it back. He won’t return my calls. I don’t want to cause a war, but a deal is a deal. Any ideas on how to remedy this? –BAD DEAL

DEAR BAD DEAL: The reality is that your brother was given something in good faith assuming he would pay you. The fact that he is trying to back out of this deal is ridiculous, especially since he will be spending far less than what your ex paid for the ring and what it is currently valued at. I would be fuming – not because of the money – but because of how he took advantage of your kindness and support and is now turning on you. I would send him a text message and make it very clear that unless he responds and works on a payment plan with you for the full amount, you will let his fiancé know within 24 hours what he’s been up to. Sounds harsh? Good. Maybe this will jolt him awake and he will want to honor this agreement if for no other reason than to save face. I would also eventually talk with him about what was going through his head when he decided to ghost you over money. If he couldn’t afford the ring, why didn’t he tell you that? If he is embarrassed, he needs to share what is on his mind and be honest with you. You can’t have a meaningful relationship based on mistrust. You can work with him and his situation, but hiding like a child is not the answer. But don’t say any of that until this money is back in your bank account, where it belongs. 

DEAR NATALIE: I am hosting Thanksgiving dinner (again). My sister and her family always come early, leave late, make a mess, and don’t contribute more than a bottle of wine. We have a large family, so it is a massive undertaking to cook for 20-plus people. While I understand that hosting “isn’t her thing,” I feel as though she takes advantage of my hospitality. Is it tacky for me to ask her to make a financial contribution this year? I spend hundreds of dollars on this dinner every year. Would I be wrong to ask her to chip in $75 or $100? Her family alone eats double that amount, easily! – DON’T TAKE ADVANTAGE OF ME

DEAR STILL HERE FOR HER: Instead of singling her family out, why not send an email to everyone that is invited this year saying that they can either contribute a side dish/dessert, or if they prefer, contribute financially? I wouldn’t demand a certain dollar amount, but I would let everyone have the opportunity to contribute in whatever way that they can. Make it clear that they are more than welcome to bring a bottle of their favorite beverage, but that the food is really where you could use some support. Sometimes, we take on so much and don’t think about the reality of what that means to us – mentally, physically, or financially. If hosting is becoming too much of a burden, perhaps rotating to different homes is a better option. While I am sure you feel resentment towards your sister, it is up to us to set boundaries for how we interact with others. She may be clueless as to how you really feel. Give her the opportunity to contribute and see what happens this year. She may surprise you. And if not? Send me another letter and we will talk about the next steps! 

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DEAR NATALIE: My husband and I have worked to save for a house for many years. This past year, we finally scraped together enough money and we were excited about the prospect of owning our first home together. In fact, it will be the first time either of us has ever owned a home. We are in our mid-40s and I never thought this day would come. Well, my stepdaughter has decided that she needs to come home. She is 26-years-old and just broke up with her long-time boyfriend. She has never held a steady job and wants to stay with us while she gets her life together. This means we will need to find a bigger house. I have suggested to her that she will need to pay rent to help us offset the cost of a larger home and a slightly bigger mortgage payment. She was really upset by the thought of that. I told her the other options would be that we get the original house we wanted and she would have to either sleep on the sofa until she finds a job and apartment, or she can take over the lease of our current one-bedroom apartment. Neither option appealed to her. I don’t think it is fair for her to assume that she can just disrupt our lives and move home on a whim, without having to pay rent. My husband – of course – is waffling. He said he doesn’t want her to “feel bad” and wants her home with us. I am frustrated because they are teaming up against me on this. How can I convince him that it is in her best interest to get back up on her feet and not baby her? She is his only child, and I think there is a lot of guilt on his end for not being around much when she was growing up. Any suggestions? –NO FREELOADING 

DEAR NO FREELOADING: I would reframe this argument. By letting her crash – for as long as she wants – and not having to pay rent, you are both enabling her behavior and therefore not helping her move her life forward. Share with your husband why creating boundaries and expectations is important for his daughter as she becomes more and more independent. You don’t want this cycle of every time there’s a breakup, there’s a knock at the door. Teaching her how to manage her finances and have responsibilities will help improve her self-worth over time. She is not a child. If he treats her as such, she will act as such. The most loving thing you can do for her – which is also pragmatic – is make her stand on her own two feet. You can assist her in that transition, but she needs to sign something that says she will move in on a certain date, contribute X amount of dollars a month while living with you, and then move out on a certain date. Stand your ground, or you will never be rid of this toxic cycle.  

DEAR NATALIE: My ex-husband and I have been divorced for seven years. During the early days of COVID, we moved back in with each other because our college-aged kids were staying with us and we all wanted to be under one roof. One night – after a few too many glasses of wine – my ex and I slept together. Neither of us had remarried since our divorce or really dated anyone seriously. I think we always still carried torches for each other in a way, but we just didn’t work as a couple. Living together again was actually really nice and I realized that maybe he just needed time to grow up. We continued sneaking around for months until our kids caught on and realized we were (sort of?) back together. My eldest daughter told me that he is planning on proposing again around Thanksgiving. She was sworn to secrecy but felt that I had a right to know since it would be such a big life change, yet again. She isn’t convinced that we should get re-married and told me that I better "not break dad’s heart again.” I had an affair years ago when she was very small because I was so unhappy. It took a toll on all of us. So now I’m nervous that he may propose, because while I do want to marry him, what if I mess it up again? – OLDER BUT AM I WISER?

DEAR OLDER BUT AM I WISER: It takes two to tango. Infidelity is often a symptom of a larger issue in the marriage not being addressed. You said that you didn’t “work as a couple” and that he “needed time to grow up.” Were you feeling resentful all those years ago, and so you cheated because you were also emotionally immature? Having the tools to communicate more effectively now that you are both older (and I hope a little wiser!) could help head off any of these old red flags. Has he grown up? Have you worked through your infidelity and what drove you to that place? Clearly, he must still love you very much if he is willing to give it another go, based on what you've written here. It is worth fighting for if you feel the same way. You could always seek counseling together prior to formalizing your second marriage together, to work on anything that may be holding you back or that caused past resentments to build. I am excited for you and this second chance of love. Remember to be honest with yourself through this process and to recognize that maybe you both needed to grow up. This can be your chance to prove that you have.

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DEAR NATALIE: My daughters are constantly fighting. I had my eldest daughter with my first wife and my second daughter with my second wife ten years later. Both girls lived primarily with me and my second wife throughout their lives. My eldest always looked at her younger sister as a nuisance – maybe because they were so far apart in age. As adults, they don’t have much to connect on – my eldest is 38 and her sister is 28. The older one married a very wealthy man and they live a fairly extravagant lifestyle. My younger daughter is more “bohemian” – not setting down roots or keeping a steady job. For the holidays, the eldest invited us all to Hawaii – fully paid. But, they recently got into a big argument and now they aren’t speaking. My youngest said she isn’t going on this trip. Her mother and I have begged her to reconsider. We want them to patch this up. My older daughter said she doesn’t care if she comes or not, which is only making things worse. My ex-wife has thrown her hands up. I don’t know what to do. Any thoughts? –CONCERNED DAD OF DAUGHTERS

DEAR CONCERNED DAD OF DAUGHTERS: It would be a shame if your daughters don’t find their way back to one another. One day, they may be all the other has, and then, family may be of more value to them. But it could be too late if they don’t work it out. You aren’t asking them to become best friends, but can’t they at least hang out a few times a year? And who could be miserable on a Hawaiian vacation? Ask them each if they are just willing to meet with you (as a buffer) for a coffee in the next few weeks to chat about things. Most likely it is a small thing that has blown up into a big thing due to miscommunications and unresolved hurt feelings. If they won’t meet with each other, you may just have to let it go. This is their path to walk and while we can try to work on relationships, we also can’t pick our family. Over time, they may realize that while they have a lot to work on, perhaps having a friendly relationship is better than none at all. Time provides perspective. Until then, just love them both and offer to support reconciliation whenever it may come. 

DEAR NATALIE: My step-daughter just had a baby and hasn’t wanted me to come and visit my grandchild yet. Her father and I divorced after 25 years together, but I have always been included in family events. I helped raise her. I’ve known her since she was 9-years-old. I am heartbroken that she is choosing to leave me out. Her father takes my side on this and we have an amicable relationship even though we are no longer together. She recently told him she doesn’t know “why I want to see the baby, I’m not ‘really’ the grandmother.” But since her mother has passed, I am the only one on her side to be a grandmother-figure. I'm not sure why she is pushing me away. We have always gotten along and had a nice relationship. How should I proceed? I want to be mindful of the delicateness of all of this, but I am truly hurt and heartbroken. Any thoughts? –STILL HERE FOR HER

DEAR STILL HERE FOR HER: Your step-daughter has just gone through the most profound transformation someone can experience: becoming a mother. Perhaps she is having a hard time wrapping her head around this and needs a moment to let it all settle in. She may be missing her own mother as well as experiencing the highs and lows of being postpartum. Give her a minute to digest it all. Perhaps send a hot meal to help ease some of the stress along with a letter sharing your excitement for her. Remind her how much you love her and how you hope to have the chance to share in this beautiful moment. If she doesn’t come around right away, try not to take it personally. Let your ex-husband speak on your behalf and see if he can help to soften the edges. In time, she may realize the benefits of having you there, as support for both her and her new baby. Tread lightly, take it slow, but keep pushing forward. Eventually, she may come around. 

Please send your questions to Natalie Bencivenga to

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