Online dating is brutal, at least at my age of 32, and looking at late 20 somethings. I can imagine that 50's looking at 40's would go a lot smoother, but the whole reason I bring this up is to warn you against falling into the trap of thinking online dating is the magic bullet these days. It's not.

What you get, as a male, is the leftovers. They're women who have finally realized that just because they have 50 new messages every day, doesn't mean they're hot shit. They're the ones who realize that 47 of those messages only came because they have a vagina. The're the ones who realize that very few of the messages they get actually come from realistic suitors. Then, still, you have to contend with the fact that they may not recognize you as a realistic suitor, and not "waste their time" replying. And, then when you get a response, it's "hey, how are you?". They put no effort into creating a dynamic dialog, and then you're forced to drive the conversation over a text-based medium that severely limits your ability to convey any flirtatious or charismatic tone. You really have to put in a lot of effort to stand out to questionably-attractive women who will most likely suddenly stop talking to you for no apparant reason.

(And then, if you do actually get her on the phone and/or meet up with her, you're quickly faced with the obvious and stark reality as to why this woman felt the need to to turn online dating.)

When in reality, you can meet these same women out on the street, and immediately stand out to them as the guy who had the balls to approach them and ask them out. It's sooooooo much easier to meet a (respectable) women in person. Trust me on this.