Dear Annie: Post-divorce dating dilemmas

Dear Annie: I’m a recently divorced man in his mid-60s. I have no children and am secure in my job. I’ve been on a couple of dates since my divorce that haven’t gone well.

One day, I ran into one of the nurses I met while I was in rehab after my stroke in 2016. We became close friends and shared intimate details about our private lives with each other. She spent many nights after she got off work crying on my shoulder and generally not wanting to go home to her fiance.

One Saturday, I ran into her in the grocery store. After sharing a longer than normal embrace and quickly bringing each other up to speed on our lives, we agreed to meet for dinner later that night. I picked her up, and off to dinner we went. Then we went to a movie. On the drive home, I ended up offering her my extra room in my town house as a place to stay until she figured out what she wanted to do about her situation. She accepted and began moving her stuff in the next day with my help.

While she was getting settled in, before going to work one day, she left me a note saying she would be late coming home from work that night. When she got home after 2 a.m., she was in tears and could barely talk. After finally calming down, she wrapped her arms around me and asked if she could sleep with me, and I said yes and went back to sleep.

She’s been living here almost a year, and we get along almost too well. We stayed in last weekend, and after we both had too many beers, we ended up having the most enjoyable sex either of us have had recently. Earlier today, she introduced me to a friend as her boyfriend while we were out running errands.

I’m conflicted about raising our friendship to the next level until I’m 100% sure I’m ready for another serious relationship. She’s got a great personality and is funny, caring, a great cook and very compassionate when need be. My major stumbling block is age. I’m old enough to be her dad. She doesn’t look like she’s in her mid-30s but like a woman much older than she actually is. I’ll also say she turns me on when she lets her hair down on her days off. (She’s required to have her hair up at work.)

Your thoughts, please! – Thinking in His 60s

Dear Thinking: Solid friendships are often great seeds from which romantic relationships can blossom. But before things can grow in either capacity, you and this woman need to get on the same page. Considering the dynamic you two have had this past year – and now having been physically intimate with each other – it’s not unreasonable for her to think you’re interested in something more serious, even if you haven’t explicitly given things a label.

Start the conversation and see where things go. Explain your reservations and ask about her expectations. Don’t pay too much mind to the age difference or what other people may think of your relationship. What’s important is that you make each other happy and are aligned in what you’re looking for. With open communication, honesty and grace, it’s very possible that your bond with this woman can reach new heights.

Send your questions for Annie Lane to dearannie@creators.com.