I joined a dating site a few months ago. There have been a few mutual initial attractions with some of the men who have on their profiles that they are widowed.
My first reaction when we start communicating is that I express my condolences on the loss of their spouse. That’s all I say though. Just something short. I don’t ask anything. I can't even imagine the sadness of losing a spouse so it would feel odd not to say anything at all.
I feel as though they don't like me saying anything. Only one said thank you. We communicated for a while but it didn't work out. The other three no longer wanted to communicate with me after my initial condolences.
Is it wrong of me to express my condolences?

Empathetic Dater

Yes and no. The yes part is that you don’t know them personally, so it could come across as false. Initially, you don’t know if this is their first step into online dating since their loss, so any comment from you could be too soon. However, we do know that it’s very decent to find an opportunity to show some understanding of the situation.

So, wait for your online interest to bring the topic up first, and simply ask him if he wants to talk about it. Or not. Once he raises it, it’s best to let him set the tone, and you follow his lead.

My husband and I have been together for 20 years, married for 14. During our marriage, issues have come up regarding my mother-in-law. She’s very old fashioned and judgemental.
I’m a busy professional and often find myself feeling suffocated by her grandmotherly expectations regarding my parenting. I try hard to listen to her and maintain a relationship.
She’s said many terrible things about my sister-in-law, such as, “she’s just after my money.” She’s my brother-in-law’s second wife. My mother-in-law went so far as to amend her will so it explicitly states that my sister-in-law will not inherit anything.
I’ve realized that this is a pattern of behaviour - she frequently spoke poorly of my brother-in-law’s first wife with whom he had two sons, saying she was a terrible mother. After they split, she had a grudge against every woman he dated and did her best to break them up. Her pattern of negativity is apparent in her current comments about my sister-in-law, who is a caring and lovely person who knows our MIL doesn’t like her.
I’ve now realized that she’s probably been bad mouthing me for the past two decades.
My question: how do we navigate family events given the climate of judgement that she has cultivated? Should I speak with her? Attempt to get her to see how she comes across?  I don’t want to hurt my husband but his mother is the instigator of all this drama.
What should I do?

Tired of the drama

Here are some choices – you could choose to understand that your mother-in-law is older and difficult, and try to keep the peace in the family; or, you could talk to a professional therapist for help with someone so embittered and angry, who creates targets within the family.

Sometimes, by standing back from the problem, and handling things in a non-combative way, you can lighten the moment.

Meantime, one of your best resources for help and information, is your own husband. He grew up with her, and is surely aware of the drama his mother causes. Maybe you can get him to share some background information to help you and your sister-in-law figure out how to live amicably with her.

Readers’ Commentary Regarding COVID boundaries with extended family (Sept. 29):

Reader – “The writer is asking how she should insist on certain rules she believes are important for protecting her children moving forward with family members who don’t feel the same way. Trust has clearly been broken when they clearly do not go along with her rules, and instead bring an unmentioned illness into the household, and allow others who are unwell to live with them. This can surely hinder further interactions moving forward.”

Ellie – As I initially replied to the writer, she and her husband were wise to create boundaries; but COVID has been a bone of contention amid many extended families, with people of all ages reacting differently. The writer loves and respects her in-laws, so I suggest they do their best to work things out, keeping their child’s health and welfare as their main focus.