Cougar teases me but ignores my advances

Roger has his eyes on a woman who he has fantasized about making love to.  Because of her being so much older than him and the fact that she is a family friend, he does not think that it is practical for them to have a normal relationship but he desires her badly.  He writes, “I feel I’m caught between a rock and a hard place with this woman, I’ve fancied her for years… And she’s known it for years too!  In a way, it would be so much easier to deal with and maybe even let go if she were to just say ‘bugger off, I’m not interested’ - but not saying anything and even to some degree encouraging me with - what I feel is - suggestive eye contact and half answers… only serve to make me believe I have a chance with her.  So with that said, the way I see it my options boil down to just two… Forget it or do what I can to give myself the best chance of success.  I’m going with the latter!  I live on my own, she knows where I live - she’s been there often enough.  We have one another’s numbers obviously so contact and location isn’t a factor that needs to be overcome.  I can appreciate that she doesn’t want to risk getting caught out - she’s smart and without wanting to sound big-headed… So am I (she knows I know what I’m doing) if it were simply the fear of being rumbled she wouldn’t be playing the games she is. Trust me when I tell you there is a definite twinkle in her eye and tone of voice when we talk, usually because what I say to her is peppered with discrete innuendos regardless of who is around.  She likes the attention, but doesn’t fancy me - as much as I may regard myself as some sort of Adonis (slight exaggeration perhaps) I have to concede that I’m not… This, unless she herself tells me - I will probably never know. It’s quite possible she simply doesn’t fancy me. But by the same token, there’s no massive reason she wouldn’t. Being honest, I’m a reasonably attractive guy who looks after himself.”

Since a woman’s rejection of a man is never so straightforward, Roger understands that.  He adds, “She maybe in a relationship that I am perhaps not aware of - this it seems is true… After a great deal of long winded tactical conversation with her friends just a day or two ago, I managed to discover she is still seeing a guy I thought she’d finished with… I thought this because she herself told me on a couple of occasions that she didn’t like him and what a loser he was and even told me of her uneventful sex life with him because of his diabetes… After discreetly questioning her friends on this subject, I think it’s fair to conclude that she is only with him because her current financial position dictates the situation.”

Roger has been told by his friends that since she might not see a future with him, and thus, she does not think that having casual sex will do any good.  Roger is aware of that, he says, and adds, “I know this is going to make me sound like a total bastard - yeah she’s hot, but not as hot as she once was… Frankly, she must be noticing a drop in interest. My thinking is I’ve observed this woman through her glory days… When she was well out of my league - but now the worm has turned, time has to some extent turned the tables. Perhaps I’m thinking, she will attempt to reaffirm her own sense of desirableness by seeing if she still has the magic of old with me (my gut feeling tells me this is my best angle).”

Roger concludes by saying, “I’ve broken the back of the work and should now just do the gentlemanly thing and wait… But I feel I need to maintain the position I’ve achieved or she’ll think I’ve lost interest (after 20 years!) and that’s the last thing I need… I’ve asked her out a couple of times now - but each time she really has been unable to accept due to work or family commitments - just the other day… I was thinking about this and texted her, “Tell me, will you ever not be busy when I ask you out?” to which I received the reply, “Who knows?”  Sometimes it drives me to complete distraction trying to work this conundrum out.  I welcome your thoughts.”

I agree with you that you should keep the effort ongoing because so far you have not received any signal from her to stop or that she dislikes it even one bit.  I guess she enjoys the attention as much as you are enjoying the chase. Now as you have pointed out in your email, it is complicated.  I guess we know a few things for sure: that she likes what is going on, she loves the game, but she is somehow reluctant/afraid/disinclined to take the next step.  The reasons could be one or more of what you have discussed above and maybe some day you will find out.

I think I will like to add a slight spin on one of the reasons that if she has sex with you, it will just be uncomfortable from there on for the two of you.  Now, that is not a problem when you pick someone in a bar and never see that person again but in this case, she and you will see each other over and over again because you are family friends.  You tell me that you have already noticed a change in your interaction with her after you told her what you wanted.  I do not think it is impossible to deal with it even after you have casual sex but maybe she is just afraid or will eventually overcome her discomfort.  I have heard from many of my readers who have secret relationships like this one and when they are in company of other people they act as if nothing has changed but when they are together, they do whatever they feel like.

So Roger, don’t change a thing about what you are doing, be patient, and keep trying.  Eventually, she will realize that you are genuinely interested in her and yield to your demands.  Considering her age she does not want to feel used and abused.