Note: This article is written by Cubby BearApproaching an older woman, just like approaching a younger woman, is very easy. Just put one foot in front of the other until you're standing close enough to talk! The hard part, of course, is having something sufficiently witting and charming to say so that she's willing to have a conversation with you. It's the second part that's much easier with older women.
Maybe it's because they've already heard every cheese-dick line already. As a rule, if you want to get into the cougar game, get rid of all your pick up lines. ALL OF THEM. They don't work. They just convince a woman that you're an immature shitbag who thinks that pickup lines actually work. I can't tell you how many times i've observed men go down in a flaming wreck after an ill-advised pick up line, only for the woman to joke with me about it after the fact.
Or a divorcee may already feel insecure with her status as a single person and empathize with the difficulty of approaching a stranger and respect your courage. It could be that an older woman just hasn't gotten hit on that much and appreciates the attention. (if she's hot, she may have been hit on frequently while married, and either didn't notice, or chose not to notice - women have this amazing ability to view the world the way they want it to work) Older, newly single women often don't realize how absolutely, hands down, smoking hot they are. This is only made worse when a woman is left by her husband for some 25 year old bimbo. I used to get criticized by my friends for dating women in their 40s and 50s, and they would always say the same thing: "She's old!" to which I would always say "Hot is hot." There are plenty of older women who are objectively hot by any traditional measure that guys look at: boobs, butt, legs, face, whatever your thing. Case in point: J Lo., Heidi Klum, Elizabeth Hurley, Kate Beckinsale, Elle McPherson, Jennifer Aniston, Sofia Vergara and on, and on, and on...... (not that you're dating Hollywood hotties, but it's not like women have an expiration date like apples. Simply turning 40 doesn't mean a woman has been retired to the trash heap of hottness)
It could also be that the woman has been out of the dating game for a long time and has forgotten the dynamic of men hitting on women. A younger, attractive, woman EXPECTS men to hit on her in a bar, at a restaurant, at work, the street, the gym, the grocery store, and pretty much everywhere else. As a result, it doesn't register in her brain that someone may be legitimately interested in her; she will just brush it off as "another creep." An older woman may have forgotten that this is a common occurrence and thus, more likely to at least give you a 2 minute conversation.
I'm sure that it depends on the woman, and it's probably some combination of all of these things. In any case, simply saying "hello" (like a normal fucking person) and making a context-appropriate comment should do the trick. By that I mean, if you're in a bar, offer to buy her a drink. If you're smart, you'll look at what she's been drinking and offer to buy the same. (If she's got a brown liquid in her glass, don't offer to buy her a vodka) If you're a restaurant, make a recommendation about what to order. I think grocery store pick-ups are weird (usually a woman is there to stock her fridge, not her lady bits) but help her find an item or make a recommendation between two brands. Compliments are nice, but be careful. You start talking about how much you love the cut of her new dress and you're going to get "friend zoned" quicker than a sailor catching chlamydia in a Bangkok whorehouse. Or even worse, she might just assume you’re gay and then you're really SOL. The main thing is to have a follow-up comment. Don't stop at "hello." She may give you 60 seconds more than some 24-year-old uptight, gold-digger, but that still only leaves you 90 seconds. Whatever you do, don't ask about her kids, her ex-husband, her divorce, or anything else that reminds her that she is supposed to a responsible adult, rather than cavorting around with a fresh piece of meat.