When they use actual stammering in a typed sentence, I immediately write them off as disingenuous. On the up side, the manipulation is much easier to see in these guys, so they're doing us a favor by allowing us to eliminate them right out of the gate.

I find it difficult to state clearly what I mean when it comes to complimenting a lady. Fearing the PC backlash or being thought of as a dirty old man like Quincy ME!
At work I sometimes have to remind some of the girls that the guys we look after are sexual creatures too, but often lack the understanding of what is socially unacceptable.

Well, I find you very sexy! There, typed it out loud.

Without knowing his experience level....I'd cut him some slack. Normally if they approach me this way, I may not be the most receptive. I like to get to know someone a bit first. Not a prude but I need more than just a warm body.

Not everyone is comfortable doing the message thing.
Some folks are shy.
Some are simply not good at online communication.
Some only do well on the phone.
Some only do well face-to-face.
And some have trouble communicating on any level !

May be generation gap. Sex was a taboo topic when he was young, much more so than after the pill (1960) and Human Sexual Response (Masters and Johnson, 1966).

Sounds kind of sweet to me. He doesn't want to offend but still make it known he finds you attractive.

Maybe just nervous..

Have to consider cultural norms in the location where someone lives. In Virginia going right out and saying that would be insta- block.
For men, it's damned if you do, damned if you don't. If we treat a woman as an equal , with respect, one gets labeled timid, if we are direct , all the sudden that lable becomes evil misogynistic pig. With most women there is no middle ground,it has to be one or the other with generally one opportunity to see if the test has been passed.
Personally I won't get overtly flirtatious. I'd like to think females are more evolved than that, and so I know the friend zone is my destiny,, and I'm good with that. At least I won't get caught up in any games.
The Me too movement has not done relationships any favours. Before thinking that it has straightened men out, consider Sweden, where they did such a good job of neutering their males over the last 20 years, that many Swedish women are now importing males from Latin America so they can get the schmooze treatment. " Don't it always seem to go, that you don't know what you've got till it's gone "

Sounds like he doesn’t want to offend you. Maybe he has tried that in the past with other women and received unpleasant reactions. I would be wary if someone started out with Hey Darling or Hey Sexy. It’s just not the style of approach that appeals to me. He wants to compliment you and not scare you off.

Shy and respectful.

Sounds like he had to muster up a lot of courage to just even message you ,Sounds like he is Shy and lacks self confidence in talking to woman,lack of experence ,maybe he has lost his wife,she may have been the only lady in his life since a teenager, But i also feel for you also as it is very hard to answer back when you do not know there back ground or where they are coming from ,where as you are very self confident ,exact opposite it seems in speech . You handled it well as you normally do ,Warm hugs

Shy and not sure how to proceed. He is older and probably not use to online interaction like this. At least he said something. I get a lot of Hi! that's it, just hi.

Shy and insecure.

I think it’s a skill to be clear and tactful and all too often those that have it are insincere. He seems to be trying to be polite, testing the waters, taking his time. The sexy word needs to wait in a friendship sometimes.

Here's the deal: A man has to speak to both a woman's brain and her heart.
If a man does not talk to her brain, she deems it lack of respect.
If he does not talk to her heart, he gets "We can only be friends"

Yet, it has never been proven that women have a sense of humor.....so tread lightly there guys

U look sexy, and much more to me

Fear of rejection.