My situation is somewhat difficult to describe but I'll try to keep it brief.  I am a 46 yo man (married) who has recently been seeing a 33 yo woman. She has known from day one that I'm married and separated and have not lived with my spouse for nearly 2 yrs now.

Despite having dated for about 4 mos now, there has been no sexual activity of any kind.  What is perplexing to me, however, is the fact that we frequently discuss sexual matters, including our shared interests in: watching porn while masturbating, our same-sex adventures (e.g, her being with women and my occasional t-girl provider hookups) etc.

I'm beginning to wonder if I'm simply an idiot here...or, am I just in one of those situations where I can't "close the deal" She insists she is sexually attracted to me, the age difference is not a problem, etc. But there's always some reason why we just don't ever get busy. As I said above, she's had interesting sexual adventures, including women at gay bars, online dating hookups (as have I, lol).

Frankly, I'm beginning to wonder if she has someone "stashed" on the side who's taking care of her needs, or she really deep-down prefers women or whatever. She seems very sexual...or maybe she's just not that into me??? OK, i know this is more Dear Abby than erotic highway, but, damn, I hate to brag...but, typically, when I've invested 3-4 mos. on a woman as sexual as this one, who tells me she's hot for me etc., usually some sex starts happenin.  All replies will be appreciated.

Dear tristater45,

It is exactly this type of question that gets addressed here on the Highway, so you are being perfectly appropriate.

As to the situation in question: have you asked her WHY there hasn't been "any sexual activity of any kind?" One would think that both of you are adults, so no need to play coy here. My hunch is that she may be lesbian, but until she comes forward and says so - who knows?

After all, sharing stories about bedding women kind of seems like a no-brainer. It is also interesting in that many lesbians HAVE had sex with men - it may just not be their orientation. So what may seem like dating to you, may seem like a deep friendship to her. This may not necessarily exclude sex, but it's certainly not on her immediate horizon, or she would have made it clear a long time ago. Some lesbians can seriously flirt with the idea of having sex with men, but somehow it never gets to that point.

Aside from the sexual orientation issue, she may just be a busy gal. So much more the reason for you to ask her away on a weekend, or set up a date in a fancy hotel with a room reservation attached to it. If she bolts - well there's your answer.

Being upfront and having a frank discussion about it seems appropriate after 4 months of trying,

The Love Goddess

You even see that mentioned in Sitcoms. If you've been on more than 2 dates, and there's no sex, then she's probably getting what she wants, and as much of it as she wants, from the relationship (companionship, entertainment, nights out on the town, etc). Time to clear things up fast, or move on.

Seriously!

I just did this with a gal I had known on and off for about 40 years and it did the trick, lickity-split!

(And I do mean lickity, if you catch my drift.)

I'd probably suggest you whip it out as well.

These things rarely just happen - she's probably wondering if you even find her attractive.  Take the initiative.

a bottle of Patron.

I have a feeling LG is right and your discussion of same-sex exploits makes her think that you and she are on the same wavelength, and it's not for a hook-up.  She may even think it's the reason you separated from your wife.

The gay/lesbian people I've known all had very close opposite sex friends.  In fact, they usually seemed to be their best friends, but there was never any sexual intentions from either person.  They'd talk about sex, like girlfriends dish the dirt, but they weren't ever having sex with each other.  You may be filling that role for this woman, even though you're interested in something entirely different.

If that scenario is off base, then you've become her friend and not her sex partner.  It's tough for guys, because most of us aren't good looking enough to sweep a woman off her feet just by showing up.  So we try to become a friend and show her that we're a great guy.  But once that pattern is set, it's easy to get viewed as only a friend, and before you know it, she doesn't want to complicate her friendship with you by adding sex into the equation.

I don't think I've ever successfully converted a friend to a sex partner once it's gone on for 4 or 5 months.   So there's a basis in fact for why the cynical amongst us saying that if you're not having sex after 3 or 4 dates, move on.

I'll give you an example.  I had a really attractive neighbor that I wanted to have sex with from the day I moved in.  We became very good friends.  She'd come up to my place to watch movies- wearing her pajamas!  We'd have margaritas at sunset after working together on some home improvement projects, we'd frequently make dinner together etc.  So after months of this, I finally asked her out on a real date and got immediately and firmly rejected.  Not only does she give me a flat out "no," she has the audacity to email me a list of 10 requirements any man must meet in order to date her.

I was so pissed off I threw away the list, and I really regret it, because it was such delusional hypocrisy and I should have framed it.  I got all the proof I needed when a girlfriend fixed her up on a date with a guy that was far less attractive than me (if I'm a 6, he was a 4), wasn't of her faith (requirement #2) and didn't meet half of the other items on her list either.

But he was smart enough to invite her to Vegas when his boss wanted his corporate jet flown out there.  And she was dumb enough to think it was his.  Her panties hit the pavement as soon as the wheels of the jet did.  She fucked him for about 4 months before she found out that not only wasn't he rich (requirement #1 on her list), he had far less money than I did! What's a girl to do?

Needless to say, I wouldn't have had sex with her under any circumstances after that, but it did teach me an important lesson.  LIke I said, I should have framed that list and put it on the wall to remind me that you can't work your way out of the "friend zone."  You're there because that's the way she views you, and barring some major change, that's where you'll stay- at least until you decide you've had enough.

Not to contradict any of the previous scenerios, which are possible...  Some women, my wifee specifically included, may be ok with thoughts of sex but in actuality have little or no sex drive.  Wifee had NO sex in the 5 years after her first husband's passing.  
When we got together, she waited for me to make the move.  She still has a low sex drive but will go along with it on occasion.  

I see the talking about sex...  as a teaser...  but not really caring one way or the other.  This could also play into her orientation...  

I think it's time to wine her, dine her, romantic walk on the beach & make the advance.  If you get rejected, then call BS (to yourself) & move on.  
skb

I see I am going to have to mention the dark side of possibilities and I speak from firsthand knowledge from both a provider that I knew who did this and a non-provider. Both were young and simply stunning. The provider I got to know because after a couple of great sessions I stopped seeing her. She called and asked why, I explained that I prefer women and only see girls from time to time. I think she saw this as a challenge and started calling me to talk. The non-provider was a girl that lived in my building who thought I was gay because I never hit on her; she was too blonde and came off as an airhead. We started talking in the elevator, she asked me if I was light in the loafers and I told her no. And that I also prefer women not girls, she called me a jerk. But she also started knocking on my door to come visit and I got to know her.  I will refer to both as one since the MO was frighten very similar.

They both would meet men at restaurants, shops….etc and start to date them without becoming physically intimate but would discuss their sexuality openly. This would go on for months; gifts would be purchased, dinners, the whole thing. The men would become sugar daddies without knowing it and if they did try to get physical, well the girls would turn on the tears about how she thought the relationship meant more than just sex and how it was difficult for them to sleep with a man because of trust/abuse/daddy issues.
I do not know how they decided which excuse to employ on which victim but they played it up. I recall that did not always work and the guy would walk but they always never just worked one guy, many targets in motion.

I also recall that they sought very similar characteristics in their victims which were more about their ability to deal with women and confrontation then married, divorced or single. What really struck me was their ability to seek out men, almost smell a victim. They would get hit on by real players all the time which they avoided because those guys would not play along with the game. The discussion about sexuality was meant to entice…promise of possible future reward if the victim continued to play along. The retelling of such exploits to me seemed to also give them a rush, I bet the actual events (Playing the victims) was even addicting.

So I caution you, ask yourself what you seek from this relationship and if it’s more than time to tell her. Be prepared to walk, never look back if she response with less. Life is short and not a rehearsal.

As the LG said in her response, she IS a busy gal...single parent, demanding occupation, etc. AND I do think that my "still married" status gives her some pause as well, since her supervisors at her job have discussed it with her, and, of course, as a single parent in today's economy, she can't be expected to jeopardize her income.

Truly, I think my married status is likely the problem...she's into me, but can't make the entire leap until we can "go public," I suppose. Thanks for all the responses to date; any and all follow-up is welcome. But something tells me a divorce petition would move things along for sure lol!

OK, so we finally got busy!!! And let me just say....OMFG!!  Maybe all those women's magazines are onto something with those articles about "sexual tension."  Some of the most volcanic sex I've had in my life (and, not to brag lol, but she reported the same experience).

Who knew that "taking it slow" actually works sometimes?