Extreme effort needed to help interrupter

Dear Annie: I have a friend who cannot refrain from trying to start a private, two-person conversation while there already is a lively group conversation in progress. I also work with “Ruth,” and even during meetings, she tries to start a conversation with the person sitting next to her. There never has been a meeting where her name is not sharply spoken in order to bring her focus back to the group. She never seems embarrassed about the reprimand, nor is she apologetic.
At first, I was tolerant of these asides, because I thought she really needed to address a particular concern at that precise moment. Now I realize it’s just a bad habit. She attempts these hijackings in every conversation, regardless of the topic. I lately have taken to thwarting her interruptions by saying, “I’m sorry, but I can only follow one conversation at a time.” I did this twice in one day, and she looked shocked and distressed.
Ruth is in her 50s, and I suspect she has ADD. I casually mentioned the possibility to her (as if I suffered from it), and we reviewed an online list of symptoms together. Although she has 90 percent of the symptoms listed, Ruth was not impressed and shrugged off the information. If I am any more direct, I’m afraid I will lose her friendship.
After 20 years of knowing this woman, she has not changed her behavior. Do you have any suggestions or advice? — Polite Conversationalist in Boston
Dear Polite: Ruth may not realize she is being inappropriate, but over time she has no doubt irritated people who are professionally and personally important to her. You were smart to frame her problem as if you also had one, so don’t give up yet.
You would be doing Ruth a favor by pointing out that interruptions of this sort unintentionally alienate people, and it would be in her best interest to concentrate more on being part of the group conversation. Admit conspiratorially that this takes a lot of effort and give her some pointers that you’ve “picked up.” (P.S.: If you don’t have the gumption to do this, be prepared to put up with her interruptions forever.)
Dear Annie: While at a recent meeting of university women regarding our city’s social services budget, one wealthy, elderly woman complained that people on welfare were a drain on taxpayers’ money. I was taken aback by her selfish attitude but stunned when she added, “There is no such thing as a single parent.”
As a divorcee, I raised children without the benefit of child support or government assistance, well before laws were enacted to track deadbeat dads. Having struggled for many years, I was highly offended by her callous remark. I would gladly have my tax dollars going to assist the poor so they might live in dignity.
What does one say to someone with such a stingy heart? —Stunned in Stratford, Conn.
Dear Stratford: Tell her, “I’m sorry you believe that, and I hope no one you love is ever in need of such help.” It won’t get through to a mind that is nailed shut, but it might make you feel better to say it.
Dear Annie: A close family member has been a student for the last 30 years. He continues to get numerous degrees in various fields. What is the proper etiquette for sending graduation gifts? Do we send one each time we get an announcement that he has another degree? This is breaking the bank. — San Ramon, Calif.
Dear San Ramon: After the first degree, all that is necessary is a nice card and your warm, good wishes. We hope with all those letters after his name, he also has a J.O.B.