What are you thoughts on my father's interesting behavior? (Details inside)

Perhaps the telephone game is the problem here. Your dad receives an email from you that he is not expecting. He’s discussing it with your sister and makes an off the cuff comment about how you must be terminally ill to send him such a nice email. Your sister doesn’t quite pick up on the nuance and relays what she heard to you, and now you’re 2 people removed from the original comment. Just a theory :)

I think it’s great that you sent your dad that email.

All my kids are grown. I have one child who is a bit more difficult and distant than the others. If he does something out of character, I might bounce it off of one of my daughters, trying to figure out if he has a hidden agenda. If your dad is closer to your sister he may have done that, just trying to process what you said. Your sister probably took it upon herself to contact you and that was her bad if she did.

I feel compelled to say that my sister and I talk pretty much every day so she didn’t call just to discuss my dad’s phone call. Sorry I didn’t make that clear.

As you said yourself, you and he are not so close. So his calling you to ask after your health, etc., could be taken as kind of a snarky move on his part, as if the only reason he would have to contact you after you sent him such a nice email is to find out, “Are you about to kick the bucket, or what?” Or, “What got into you to send me a nice email out of the blue? Something must be very wrong.”

It’s time for another email, or better yet a phone call, or best of all, a visit in person and a hug and a long conversation to say, “Gee, Dad, apparently it’s not too late, maybe we can have a closer relationship. Whaddaya say?”

PS: Best not to ask for money at that meeting, unless you really need the money and have given up on the relationship.

All I can think is that he was so startled by your email that he wasn’t sure what to think. I’ve been startled like this before and have turned to someone else (usually my bff or husband) to act as a sounding board. As @Judi said, he may be trying to process it.

Sometimes we have done something or created a perception of ourself that is false. Is it possible that there is some gross misunderstanding about you that is shared by your family? I wouldn’t get angry about it, but would try to figure out what it is and correct it.

What’s coming to mind is a story by Edith Wharton, where the mother was divorced and shunned by society, forced to live abroad. When she finds out about her daughter’s divorce, she immediately rushes to her side to show her support. However, when she gets there, her daughter is surrounded by friends and everything is good. The mother however, is packed off to supper in her room, cut off from socialization, because over time, no one remembered why she was shunned, but she simply became the woman that everyone shunned.

In families, people get labeled for odd reasons. In my family, I am “the smart one”. My sister is “the attractive one” and my brother is “the lazy one.” I cannot be the attractive one, and neither can my brother. On the other hand, I can goof off and procrastinate, and I’m never considered lazy. My brother, on the other hand, no matter how hard he works is still lazy and never smart. My sister is not considered smart, but has finally earned “compassionate” which is funny, because she can be very difficult and critical.

Perhaps you “are” something that you’re unaware of… If you can figure it out, I would suggest not getting mad about it, because it may only confirm it. But start with your sister. The fact that your dad thought the email was something she would find funny hints at her having an idea as to what “it” is.

I think you need to call him more often.

It seems this incident has provided an opportunity for you to get closer to your father. How about taking him to lunch or dinner and telling him how surprised you were that he was surprised you said something nice to him.

Tell him that you will need to say nice things more often.

Lots of great answers. I’d give anything to be able to talk to my mom or dad again.

Maybe it is as simple as him not being able to take a great compliment.:)
I wrote my dad a letter in my 20’s to let him know how I felt about him and why.
I felt kind of funny giving it to him because we were not especially close at the time.He thanked me for it and that was it,or so I thought.
Years later,my mother later told me that he had cried when he read that letter and kept it in a special place in the dresser.
You just never know…. ;)

What I think about it: He appreciated your email so much he was dumbfounded.