TaxMan Posted May 8, 2017 Posted May 8, 2017 Hi, This is my first post, so please be gentle! LOL I am 42, divorced about three years after a 12 year marriage, with two kids I have half the time. About a year after my divorce, I was in a relationship for several months with a woman I worked with that ended amicably about six months ago. We are still friendly but we don't really hang out or anything. She was quite a bit younger than me (31) and wanted a family. I'd already done that and didn't want to do it again, so that ended. Right after that, I met a woman through mutual friends who I really, really liked. She's just a few years younger than me and we hit it off immediately. We exchanged contact into and started spending quite a bit of time together. At first, it was just as friends, usually in groups, but she was always very flirty with me, touching me constantly and always putting herself very close to me every time we were together. I reciprocated, but I admit I wasn't 100 percent ready yet for another relationship, so I didn't know exactly how to proceed. I let her know I was not really ready for a relationship, but also that I really liked her and wanted to keep seeing her. So over the past several months, we started spending much more time one on one, like two or three times a week, and her flirting got much more obvious. She started touching me way more often and dropping obvious sexual references into conversations. It was very clear she liked me, and I let her know the feeling was mutual. Still, I was a little wary of jumping from one relationship to another, I didn't want her to be a rebound or a one night stand, I really like her and she seemed to be worth way more than that to me. Also, I am accustomed to taking a while to get to know someone before jumping into bed with them. Still, each time we'd go out, I would get a little bit physical, first just kissing goodnight and then eventually fooling around a bit more than that. No sex though. Yet. The past couple times we've been together, I get a strong feeling from her that she is frustrated that we haven't slept together yet. It's been about three-plus months since we started seeing each other, though at first I was just out of a relationship and not even really ready to date. I know she's not seeing anyone else. She's never been married and doesn't have all that much experience in the dating department. She's in her late 30s and doesn't want kids, which is perfect for me. Now I feel ready to take things to the next level, but am not sure if I missed my window. Should I talk to her and tell her I am ready or just make a move and hope for the best? (Back story: The woman I was seeing from work made the first move on me, so the last time I had to figure this stuff out was maybe 15 years ago when I started dating my ex wife. I feel very out of practice in that department.) Any advice? Did I miss my chance? Can I just sit her down and say, OK, now I'm ready? Or just make a move and hope for the best? Thanks.
central Posted May 8, 2017 Posted May 8, 2017 All you can really do at this point is make a move and see if she responds. IMO, you're much too slow at developing intimacy, but you have to do what feel rights to you, even if it greatly limits your chances. 1
Grey40 Posted May 8, 2017 Posted May 8, 2017 I think you have to make a move. Only way to find out if the window is closed. It seems that the window is open much longer for older women because they usually have far less options than younger women, so just go for it 1
Author TaxMan Posted May 8, 2017 Author Posted May 8, 2017 Thanks all. I honestly don't think she'd keep seeing me and continue dropping hints if the window had closed for her. And, I agree, I've taken too long here to get around to making a move, but I wanted to do it when I was ready and not just because it was the third/fourth date or whatever. I was not ready before and that would have probably meant the relationship wouldn't last. Just a thought.
preraph Posted May 8, 2017 Posted May 8, 2017 I think you've talked quite enough. Have sex already. Make it a special night, romantic dinner, ask her home for a nightcap, and makeout on the couch but just don't stop. Have a condom nearby. 3
Author TaxMan Posted May 9, 2017 Author Posted May 9, 2017 I think you've talked quite enough. Have sex already. Make it a special night, romantic dinner, ask her home for a nightcap, and makeout on the couch but just don't stop. Have a condom nearby. Good advice. Thanks preraph. I admit to being a little bit nervous because even though I have had a relationship since being married, this is the first one where I actually feel like there could be a future, and I really want there to be one, so I don't want to screw it up. But then I remember that I could screw it up by not doing something as easily as I could by doing something. So what do I have to lose?
smackie9 Posted May 9, 2017 Posted May 9, 2017 You are getting way too far of yourself......there are no guarantees in life, if it doesn't work out, oh well, move onto the next opportunity.
Author TaxMan Posted May 9, 2017 Author Posted May 9, 2017 You are getting way too far of yourself......there are no guarantees in life, if it doesn't work out, oh well, move onto the next opportunity. I guess that's part of the issue. I've been out of the game a while and have never really been a serial dater even when I was younger, and I really have to like someone a lot before I get to this point with them. So it's not as if the "next opportunity" that is as good as this one is a guarantee. People I like this much don't come around all that often. You may be right, I may be getting ahead of myself, but I am not really the type to just jump from one to the next and just think, "oh well." I know there are people who do, and that's fine. That's just not me.
SevenCity Posted May 9, 2017 Posted May 9, 2017 I guess that's part of the issue. I've been out of the game a while and have never really been a serial dater even when I was younger, and I really have to like someone a lot before I get to this point with them. So it's not as if the "next opportunity" that is as good as this one is a guarantee. People I like this much don't come around all that often. You may be right, I may be getting ahead of myself, but I am not really the type to just jump from one to the next and just think, "oh well." I know there are people who do, and that's fine. That's just not me. The fact that people like this don't come around that often has nothing to do with your need to build up for a while before having sex. People like this don't come along often. Period. I've slept with a lot of women and the same thing happens to me. I've been dating for 8 months and finally found one I wanted to make my gf. Tough love time. Man up and bang her already! Eventually she will tire of your platonic relationship and move on to a guy like me who will bang her in no time. Don't let that happen, plant your flag now. Worst case you have sex and it doesn't go anywhere. That's a pretty good negative side if you do it. 1
Author TaxMan Posted May 10, 2017 Author Posted May 10, 2017 Worst case you have sex and it doesn't go anywhere. That's a pretty good negative side if you do it. Good advice. You are right, obviously. What's the worst that could happen? I am one of those people who tends to play out the worst case scenario in my head until I psych myself into thinking the worst is going to happen. I think I just need to relax and let it happen. It's pretty clear that we both want it to happen, but it's also very clear that she wants me to be the one who initiates it, so I just need to get over myself and get it done.
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