This room is dedicated to those who are facing the challenge of raising children without the support of a spouse. This is a place to share ideas and lend mutual support.
Saint Rita is known to be a patroness for abused wives and mourning women.
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I don't know you, but my first instinct is to say "Be yourself", unless being yourself makes you sound or look desperate or weird, which I doubt. Men are people too. If you think he is really interested in you though, perhaps you should let HIM get the courage up to make the first move. Of course there will always be someone to disagree with me, but when he does make that move, my advice is to just be you. Eventually you are going to let your guard down and be yourself anyway, so why start out being something that you are not?
May God's blessings shine on your choices, and may you seek His divine will in making them.
I'm not sure why you would feel shy. Your appearance could be enough to cause a gentleman to stammer. Guess you'd be even then.
Seriously, you have an advantage insofar as you have seen this fellow in person and discovered he is a CM member. A bit older? Depends upon how much that "bit" is, but even so, if it doesn't bother either of you, you're off to a good start. Another advantage is that both of you are looking for that special someone. You have two ways to approach him -- in person or via CM messages. There's a chance he's not a paying member, and, if that's the case, he wouldn't be able to respond. But it still could be an icebreaker in person.
If you see him at Church, you can greet him with a friendly smile (as you have done already). Just talking to him in a casual, friendly manner doesn't brand you as desperate, weird, or needy. Perhaps he is a bit shy, too, and is hesitant to take that first step. Nothing wrong with striking up a conversation -- about the day's homily, the readings, talking about the pastor or the Church's physical attributes, or asking about Church groups. Try to relax -- breathe, relax and repeat as needed. Perhaps during the initial encounters, you might simply offer a friendly "Hi" to him. After a couple times doing this, you can progress. If he is a true gentleman, he'll treat you in such a way that you are comfortable and at ease. You can even admit being shy and let him take the cue. Perhaps this is something that won't work out, but if you two don't do anything you'll never know.
You go, girl!!!