Why not ask? Because it’s probable that will end everything.
Now, if the OP wants something more than what she has, that may be the best outcome. However, if she enjoys the relationship they have and would like to continue it until something better comes along, it would probably be better to say nothing.
I think there is a middle ground and she doesn’t have to outright ask about their relationship. Less risky would be to discuss his general goals in life and how he sees or hopes for in his future…living alone, a relationship, travel, and so on. It could be that he isn’t seeking a long term romantic relationship with anyone and is only seeking friendship (not just with OP but with any person). It is hard to tell based on what was shared if this guy simply isn’t seeking a romantic relationship generally speaking, or just not with her. It could very well be the former and has nothing to do with her.
Here’s the thing. The OP wonders whether it could become something. If she tactfully puts it out there and he says he is not interested then she can remain friends if she likes. If he decides he doesn’t want to be friends with someone because she may want to date him then okay. The best part of being 50+ is being open and vulnerable and direct in a classy way. Shy or not. JMO
OP, count me as a guy who was always 100% clueless when a woman was being subtle. I only ever dated women who were being direct. Still, there are ways to bring the subject up without adding any pressure on him to escalate.
Remember, in flirting, the need to be 100% truthful goes out the window. Next time you are alone, tell him you had a dream about him last night (keep it PG, “took me in your arms” or “kissed me on the neck”). You really need to gauge his reaction. If he smiles, you can escalate. If he looks like a deer in the headlights, you can backpedal.
I really think he is interested and just waiting for a sign. “Buddies” don’t bring flowers.
That may be PG to a guy, but doesn’t seem like to to me. But I am with you that guys can be super clueless and sometimes need a little nudge, and that the flowers may mean something.
One day after you have done something together, can you just say to him, “You know, I really enjoy being with you!” (Not “I enjoy being your friend” and not “I enjoyed our time today”, both of which are weaker.)
Look at him directly when you say this, and smile warmly. See how he responds.
Even if he only reflexly says, “I enjoy being with you, too”, he may go home and cogitate on what it means that you both enjoy being together so much.
My husband says there is no way he’s not interested. He thinks men don’t spend time with women they aren’t interested in. They always are thinking about it, even the shy ones.
How do you handle the check when you go out?
I haven’t read all the posts, but my first thoughts are: He has some ED issues and is afraid to even try intimacy. Maybe that’s why the earlier relationship fizzled.
Maybe you could write yourself a script in a way that makes it very clear that if he isn’t interested romantically, his friendship is very important to you. Of course the yentas of CC will be happy to help with the scriptwriting.
As a male in this age group, I agree with eyemamom’s husband.
I would ask in a low key kind of way, just that you sometimes wonder what it might be like to move the relationship fin a romantic direction. If he is not interested, you could back-pedal and say you also think you’d be better just as friends.Is it possible he thinks you aren’t interested because you are widowed? If another woman comes along you could lose him as a friend anyway, which would be a shame if in fact he is interested. As others have said, having this friendship may make you less open to meeting a possible romantic partner. Good luck!!
All of us are guessing here and we don’t experience the subtleties but to me it is very telling that both people are shy and that he brings flowers. Flowers are a sign, a type of language that even this shy man can speak. Be careful, don’t don’t waste this opportunity either!
I once got in trouble for giving a flower to a male friend on his birthday. He read all sorts of things into it. My future H wasn’t pleased! And it wasn’t a red rose either, it was a bird of paradise. Flowers can be trouble!
I guess we are all different, but when we are in our 20’s or 30’s and we are starting a relationship are most of us more likely/willing to just enjoy the ride and wait for things to naturally happen? I mean, in a reasonable amount of time ? Doesn’t that first kiss or definite sign of affection happen unplanned, not because it was negotiated or on the timeline?
What’s wrong with OP with this type of movement in a relationship if you’re 60??? He obviously enjoys spending time with OP (unless she’s just a fabulous cook! 
) so that’s all good and healthy. If you have the time, take the time.
Don’t discount being a fabulous cook as a way to coax someone into a relationship!
^^^^
Absolutely. During my D’s first year at boarding school all the new freshmen were encouraged to look for ways to make the transition easier for their classmates - find ways to make others feel at home at the school. D decided that the guys must miss their mom’s baking, so whenever one of the boys in any of her classes had a birthday, she would bake brownies and bring them in to celebrate with the whole class. She was always very popular with the boys and I always attributed it to her baking those brownies freshman year.
What if he’s interested and you don’t make a move and lose him to someone who will? That would be a shame. I don’t think he’d bring flowers to dinner unless he was interested. It seems like he’d be afraid of leading you on.
I would definitely start sending him some signals – hold his hand, sit close to him on the couch, hold his gaze while you talk – anything to reduce the physical distance between you. There are other things you can do to express your interest. You can invite him to dinner (at a formal, date like restaurant) then go to a movie (romance or comedy). At the movie, you can put your hand on his without worrying if it’s awkward.
When he comes over to eat, make a special effort. Eat in the dining room, use cloth napkins, ask what his favorite meal is and make it. Instead of just making plans for next week, start making long range plans (next month, in the spring, etc.) that include the two of you. Is there a new hiking trail you could try? Or a concert he might enjoy? Throw out a couple ideas and see how he reacts.
Good luck.
But isn’t this kind of the most exciting part of any relationship? All the uncertainty of where it is going and all the unexpressed romantic tension. Just being together no matter what you are doing is still an “event.” If I could “bottle” anything, it would be that feeling you have in a new relationship.
My advice is to enjoy what you have and let things unfold naturally.
I’m also into letting things unfold naturally. Still, I find it unusual for a male/female “friendship” where one (or perhaps both) parties have a romantic interest, to have had no physical contact in six months. In some respects, that is refreshing (particularly to observe in a man). Still, I think it is uncommon. That leads me to believe that the man either may not be seeking more than a friendship (with anyone), is too shy to make the first move but would welcome a move on her part (she can start small with holding hands, head on shoulder if they are sitting on couch), etc., is simply not ready for sexual intimacy (has not dated in a while? has some sexual issues?), or something else. Again, I don’t think she needs to discuss the relationship and just let it unfold, but if she is interested in more than friendship, she could make subtle moves in that direction, as well as suggest longer activities like a getaway or something down the line, and gauge his reaction. He may welcome it and is too shy to suggest it himself and is not used to dating, but nothing is really so risky to do that. The fact that he is spending so much time with the OP is a good sign that he really enjoys her company and the connection they share. The flowers are a sweet gesture that is also positive. He seems like a sweet man and at least is not just seeking sex. But it is hard to ascertain if this man is looking for a romantic relationship in his life or is happy just with some companionship. Seeing how things evolve is a good way to go about it. Still, no signs of romantic engagement or physical touch is unusual in six months for anyone who would like it to be a more romantic relationship, even 60 year old men. But everyone is different.
One thing that makes me infer that the man is possibly interested in a romantic relationship is that he broke it off with another woman soon after meeting the OP.
To the guys out there: I don’t know … I’ve had close male friends where I’m fairly sure there was no romantic interest. And I’m reasonably attractive … (At least I used to be. Who knows, now.)
As a single woman who has not started dating since divorce I would be extremely interested in hearing more about that view (that men wouldn’t be hanging out with women they are not interested in). That can’t be true …
You make it sound like, for women with straight, single male buddies, any one of those male buddies would be hers for the taking. I KNOW that is not true.
I do talk to my male buddies abt their relationships with other women. MAYBE they’d be willing to sleep with any of the friends they hang around with, but have a relationship with? Fall in LOVE with?
Nah … You are selling us a fairy tale. Guys hang out with attractive women they are not prepared to fall in love with. Pretty certain of that.
I don’t think OP’s question is: would this guy sleep with me?
That’s not to say that THIS man might not be interested in a loving, long-term relationship with this woman. But can we infer it from the fact that they are hanging around together? Don’t think so …, (but nice fantasy …)
Men, please weigh in! And ladies, please consult the hubbies. Enquiring minds want to know!