I haven’t heard “Bossa Nova” in YEARS…like over 20.
I’m 61. For my playlist, unless they share a specific genre of music, Beatles, Crosby, Stills & Nash, Beach Boys, Simon & Garfunkel? The Turtles…just to be silly.
My line might be: " Just trying to check things out here. I love being good buddies, but occasionally the heart wants a little more. Am I off base in even thinking in this direction? Our friendship is more important than anything else."
Personally, I’d avoid subtle gestures, increased touch. He may be confused and then really not know how to proceed. Isn’t there a lot of emphasis on verbal consent? If hard at 60, just think of those expectations for a 16 year old!
I have few good guy friends. Since my divorce, some of those friends have picked up on their contact with me. I am hesitant because I have been good friends with some of them for a long time and I am afraid to ruin our friendship if relationship didn’t work out. As most of us know, many romantic relationships usually end at some point. OP should think hard about what she wants. Sounds like they have something good right now.
If the friendship is strong, then it should survive an inquiry about something more, even if the other person is not interested. At a minimum, he’ll be flattered. Or perhaps he will be interested in something more.
As long as you use honest words and don’t come on too strong, I can’t imagine a bad outcome.
He brings flowers. That seems encouraging to me.
Granted , this was over 20 years ago , but my husband was a bit on the shy side himself when we first started hanging out. I tried to get him to loosen up , but he was really slow at picking up on the signals I was sending. I am not shy , so ultimately, I had to make the first overture. I am glad that I did because I don’t know if he would have , and I may have given up.
We started out as friends too, with the shared experience of being newly divorced with young children
I already know the 3 songs on the seduction playlist. But they are specific to the particular individual that I am not in the market to seduce right now and will never be since I’m a happily married woman, but would have proven very useful in an alternate universe :-).
I’ll just say - the time to hesitate is through and leave it at that.
There wouldn’t have been any seductive music for my husband…he is hands down the most musically challenged and clueless person I have ever met.
So we’ve established that Pizzagirl is a Doors fan. Beyond that, it is interesting to see the diversity of opinion here that is very similar to what I’m trying to sort out. I really do think he’s a wonderful guy with whom I share a number of interests, and perhaps most importantly a similar sense of humor, and despite the “break up risks” that oldfort suggests makes me think it’s worth it to try to clarify what it is we’re doing. I have a couple of big fears…1)He will be freaked out if I pose the “possibly something more” question. 2) He is a smart, kind, funny, generous man who seems unlikely to stay single for too long given the ratio of available men to women in our general age group. If I end up in the friend zone I’m unlikely to get remotely as much of his time if he has an actual girlfriend, plus she could find it weird if he continued to do the things he currently does with me. So, I will definitely work on how to talk to him about this. I am far braver in email than in person, but I know this should be a face to face conversation.
Good luck. Our thoughts are with you. Let us know how it goes. 
Nothing to add, though I love this thread! Good luck @Anxiousmom1! Trust yourself.
No suggestions here because I am not 60 and have not dated in 30 or so years, but kudos and good luck to the oh so brave OP!
I’m excited for you! Good luck!
I wish I could edit my previous post…my husband is clueless about music only.That made him seem terrible and he isn’t at all
I just read an article about shy people using eye contact to flirt. Four seconds.
Seriously, what type of music do you two like? You could potentially play certain songs and comment on the words and see where it takes you. I’m not necessarily a huge country music fan, but there are certainly country songs that express these types of emotions. (My previous Doors reference aside, my other 2 songs on this imaginary list are country - one by Emmylou Harris and one by Willie Nelson.) Are there songs that make you think of him?
What’s the harm in just playing this out a little longer and see if things become more obvious one way or another?
If you really value him as a friend, I’d wait for things to naturally play out so that you don’t lose that “friendship”.
Sounds like the harm is that there are a lot of other single women around.
If he’s looking at other single women, then he’s probably not interested in a lasting relationship with OP. Unless he’s just looking for intimacy.
I’d try to keep the conversation light and playful at first, until you get a very good idea of where it is going.
I hope you’ll report back on how the conversation goes! Good luck!
The things you’ve written sound encouraging–broke up with prior GF shortly after you started your friendship, flowers, dinner at your home, lots of time together.
Good luck! Keep us posted!