Dear Annie
Familiarity or True Connection?

Dear Annie: I wanted to follow up on a letter you published on June 21, 2025, about my complicated relationship with my sister-in-law, who I started to develop romantic feelings for after the death of my wife (her sister).
Since your response, I had a long and emotional conversation with her. Things had been awkward between us ever since we nearly crossed a line a few months ago. It felt important to finally clear the air, and I’m glad we did.
After talking for several hours, I walked away believing she truly cares about me for who I am — not out of convenience or grief, but genuine affection. The trouble is, I’m not so sure about how I feel. Do I love her as her own person, or am I clinging to the parts of her that remind me of her sister, my late wife? That question keeps me up at night. I care for her deeply, but I don’t want to commit to something as serious as a relationship if it’s rooted in comparison or nostalgia. It wouldn’t be fair to her — or to me — if I realized years down the road that I had confused familiarity for love.
At the same time, she has formed a powerful bond with my son. She’s been there for him in a way no one else has, and she’s become a steady maternal figure in his life. The two of them adore each other. Because of that, we’ve agreed to an informal co-parenting arrangement where he stays with her every weekend. There’s no legal agreement involved — just trust. For now, this feels like the healthiest balance.
Through all of this, I’ve also come to a personal decision: I won’t marry again while my son is still dependent on me. As uncomfortable as my dynamic with my sister-in-law has been at times, I can’t imagine bringing someone new into our lives who doesn’t already share a meaningful connection with him. It just wouldn’t feel right.
I’d love to hear your perspective. Am I doing the right thing by maintaining a close, non-romantic relationship with her for the sake of my son? And how can I be sure my uncertainty isn’t hurting her more than helping her? — Torn and Trying
Dear Torn and Trying: Thank you for the update. It sounds like you are approaching this very delicate situation with honesty and compassion, which is more than many people manage.
You are wise to take your time and question your feelings before moving forward. Love built on grief or familiarity is not the same as love built on true connection. If you are unsure, it is right not to make promises you cannot fully commit to.
Your co-parenting arrangement sounds thoughtful and respectful. As long as you both remain honest and communicate clearly, you are giving your son the love and stability he needs, and that counts for a lot.
Keep leading with kindness, and trust that clarity will come with time.
“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 http://www.creatorspublishing.com for more information. Send your questions for Annie Lane to dearannie@creators.com. COPYRIGHT 2025 CREATORS.COM