ANNIE LANE

Dear Annie: My best friend and I, both 54-year-old females, met two weeks before kindergarten. Except for a couple of years, we have stayed friends throughout our lives. We see each other every few months when I’m in town for a doctor’s appointment. Since last year, we’ve been going to concerts and a couple of comedy shows, and we attended our 35-year high school reunion.

She’s always been a drinker, but it’s gotten extreme to where I don’t like being around her because she gets belligerent. And her drinking has only gotten worse since her mom passed away. I honestly don’t know how she even remembers the events we attend. She has paid for both of our tickets to each show, which I’m grateful for, but I honestly don’t know how many more I can attend with her.

With her mom’s passing, she did inherit a sizable amount of money. But the last concert was when things got weird. She kept talking about how she could change my life financially and I could work for her. To be totally honest, it really got under my skin and I felt very uncomfortable with the conversation, so I went to bed. I got up and left the next day before she woke up because I didn’t want to see her.

Being best friends for 50 years is pretty amazing, and I love her, but I’m not going to be her employee. I honestly do not know how to even approach her about everything. But I also do not want this to end our friendship. — Feeling Confused in Kansas

Dear Confused: Fifty years of friendship is incredibly special, you’re right. That said, even a bond that deep doesn’t mean you have to tolerate behavior that makes you uncomfortable.

It sounds like the heart of the issue stems from her drinking, so that’s where I’d start. When she’s sober, let her know you’ve noticed she’s been drinking more since her mother passed and that you’re worried about how it’s affecting her. This conversation could make all the difference or none at all, but either way, you’ll know you’ve said what you needed to. From there, you can set better boundaries and stick to them.

Instead of concerts and long nights out where drinking can spiral out of control, try shifting your time together to things like coffee or lunch — daytime outings that don’t revolve around alcohol.

As for her comment about changing your life financially, it sounds like the alcohol was really the one talking that night. She probably meant that to be generous and supportive, but it came across differently to you. If it’s still weighing on you, bring it up now so you can clear the air of any resentment. A friendship like this should be strong enough to handle the hard conversations, though she might have to become completely sober before your relationship can get back to where it was.

Dear Annie: I’m a brokenhearted Nana who could really use your advice.

I have a 10-month-old grandson whom I adore, but I’m not allowed to kiss him — not even on the back of his head. Recently, in a moment of pure affection, I forgot and gently kissed the back of his head. It was instinctual. I love him so much, it just happened.

The reaction was swift and harsh. I was scolded and now I’m not allowed to hold him unless he’s sitting on my lap, facing away from me. To make matters worse, I’m only allowed to see him every other weekend for two hours, and someone has to be in the room to supervise me the entire time.

I’ve tried to talk to my son about it, but any attempt leads to an argument or a shutdown. I feel like I’m walking on eggshells just to be near my grandson, and my heart is breaking.

Is there anything I can do in this situation? I feel so lost. — Heartbroken Nana

Dear Heartbroken: I can feel the love and the pain in your letter. This situation sounds heartbreaking, but it’s rooted in something more than just that one kiss. Many new parents today have firm boundaries, often tied to health concerns or parenting philosophies. Right or wrong, it’s their call.

For now, the best way to stay close is to respect the rules, as hard as they feel. Show your love through gentle presence, patience and consistency. In time, as trust rebuilds and your grandson grows, the restrictions may ease. Let your son know you’re willing to follow their rules because your priority is staying in your grandson’s life. Your love is clear. Let that be your guide.

Dear Annie: You recently offered advice to a woman in a retirement home who was struggling to make new friends, encouraging her to keep trying, as connections often take longer to form later in life. I’d like to offer a different perspective — and ask a question that’s been on my mind for years.

I’m 79 years old and have been single for nearly four decades. While I’ve stayed close with a handful of longtime female friends — some of whom live far away — I’ve found it nearly impossible to make new female friends at this stage of life. Why? Because women in our age group can be extremely territorial, especially when it comes to men.

It seems like every social situation is colored by this subtle tension. Even when old friends visit, they often leave their husbands behind or are wary when I visit them. There’s this quiet fear that any woman, especially a single one, might be seen as a threat.

Do you think it’s worth trying to form new friendships with women my age? — Still Hoping for Connection

Dear Still Hoping: You’ve hit on a truth many are reluctant to say out loud. In some circles, women of any age can be territorial, especially when a single woman enters the picture. It’s often rooted in insecurity, not malice.

But don’t give up on your peers entirely. Not every woman is guarded or threatened, and there are still plenty who’d welcome a sincere friendship.

“How Can I Forgive My Cheating Partner?” is out now! Annie Lane’s second anthology — featuring favorite columns on marriage, infidelity, communication and reconciliation — is available as a paperback and e-book. Visit www.creatorspublishing.com for more information. Send your questions for Annie Lane to dearannie@creators.com.