If I was you I would be patient and see what happens. From my experience lately the men still like to feel like they are the ones doing the hunting so to speak. If after a while you have not had any interest from him, then I would give it a try, but wait a while first to see whether he shows any interest at all.
Men can easily be scared off by a woman who seems to eager. JMHO

Thanks for the advice New. I hear so many conflicting opinions on this subject. As I said in my post, as a young woman I wasn't assertive with men. But then I look at the kind of men who did pursue me (emotionally unhealthy ones), and I think maybe I should do the picking this time! :)

I say the Ladies need to always or often do the pursuing, and do the first contact too.

An aggressive man is not a healthy sign, and an aggressive woman gives her the position to cut it off whenever she chooses.

I am 56 and I feel that the Ladies do not want me to come-on to any of them, and us older people (male and females) have far more restraint and reserve, so us Men really are expected to behave like gentlemen to the Ladies.

For an older Man to approach (confront) the Lady just opens up the possibility of lots of unnecessary problems. Some times I can make the first move - but it needs to be done very delicately for a Man, while the Ladies seem to have a stronger position in starting out a relationship - because it is easier to STOP it when you are the one who starts it.

You finding an old High School friend on Facebook, where the guy's Facebook page says that he is single - then a private message seems like a perfect way to get started.

You could start out less intense and just ask if he remembers you from the High School, and proceed from that.

Thanks for the advice, Booky. I haven't contacted him yet. I'm still debating whether I should. He lives two states away, and I'm not sure that I want to initiate a long distance relationship. Your response gave me food for thought. I hadn't considered that men may want the woman to contact them so that they don't appear too aggressive. I'm still figuring out this new male/female relationship thing post-divorce. It's certainly different than it used to be when I was 21! I must say that I'm looking forward to spending time with a man who is a gentleman this time around! (Your response gives me hope :).

Have you corresponded by messaging and just chatted to him on FB in a friendly way. Asking how he is doing and what he has been up to etc?
That may be one way to start breaking the ice, and maybe open a door for him to make some effort to communicate with you. Just a thought.

New, I haven't made any contact with him yet, other than "liking" a couple of his postings on FB. I feel really akward about messaging him because I'm just not sure what to say. We weren't friends in high school, and he was two years older. I suppose if I keep it light and friendly it shouldn't scare the bejeebers out of him :).

HealingT: From where I sit, I think you are overthinking this waay too much. You knew each other (sort of) years ago and IMO there's nothing wrong with sending a "hello, how are you?" message. You don't know until you try and being FRIENDLY isn't a bad thing. Just go on and do it! You'll never know if you don't say something -- it could turn out great or it could turn out to be nothing at all. Nothing ventured --nothing gained. This is 2012 -- and we're sure not in Kansas anymore. xoxo

Kathi, thanks for the kick in the shorts - I think I will send him a light and friendly message this week. Also, you are right - I do tend to overthink things sometimes. ( When I was 16, my best friend used to tell me that too :)
Hugs,
T

HealingT: Overthinking is LEARNED BEHAVIOR. You can learn to stop it! Now get on there and SEND THAT LIGHT, FRIENDLY MESSAGE to your old school acquaintence and let us know how it turns out! xoxox

You should message him first!

If it were me, I would be flattered!

I did it - I actually sent him a short friendly message (3 sentences). Nothing too heavy. He messaged me back with a short friendly response. Not sure where to go from here with the messaging, but I feel like I've taken a step in a positive direction. I've learned that I CAN go out of my comfort zone to initiate contact with men. This was a confidence building exercise, if nothing else, and I really appreciate all of your encouraging comments.

G'day Healing,

I am a bloke 58 years old and about 3 years ago, I found myself in a similar position to what you are in now.

The "rules" of the game have changed dramatically since we were young.

I can tell you that without a doubt, any man being concated by a woman is a huge ego boost for us. We also go through the low self esteem stuff and as often as not, don't initate contact for fear of rejection.

You have made the first steps and they have been well recieved. Bloody good on you girl!

Try not to overthink stuff, say hello from time to time and let the conversations grow from there. I promise you that they will. If he is in any way interested, you will know soon enough.

Good luck honey!

Mick

Mick - thanks for the kind words of support. I'm definitely learning as I go with this whole dating thing. It's kind of fun and scary all at the same time. :)
Hugs,
Tracy

I couldn't agree more with hairmick. I am personally quite flattered when a lady expresses interest. I have always been shy with chicks going back to high school, and it's really nice when the woman breaks the ice.

For older men, a lot of the time we assume a woman from the late 30's up is probably either married or in a happy relationship. It's terrific when we find a single woman from roughly the same age group. I would go ahead and contact him.

Whatever is the problem? Go ahead and ask him and stop thinking about what he'll think. If it matters to him, he wouldn't be the guy for you, isn't that right?