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Crossroads . . .


Redhead14

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I am divorced for 6 years and was engaged for two years before my fiance died in June of 2014. I have been on the dating scene again for a few months now. I have completely accepted my fiance's passing and comfortable with dating.

 

I am now seeing two men. The first one has been moving "slowly" which is a good thing. He has been clear about his interest in me in a direct way, however, due to our schedules we have only had dates that were spread fairly far apart. He works 11 to 7 and about an hour away so during the week it's difficult to meet. He is not seeing anyone else and has given me weekend dates so I doubt he has time for anyone else besides me. I have told him that I like him very much, but because of the space/pace of our dating pattern, each date almost feels like a first date in term of feeling comfortable. We know alot about each other, but there's still that "newness" feeling. We have not been intimate beyond kissing and even that is still somewhat awkward. But, I really like him.

 

Anyway, in the meantime, I've started seeing another man who has been very clear about his interest in me. We've had two "official" dates that lasted several hours and we meet a couple of times per week at our favorite after work place and have been spending a lot of time together for the past two months. We do not get drunk, we have a couple of drinks and have our dinner there. We usually leave around 8:30. I am very comfortable with him and he is extremely attentive, but not in a "creepy" way, he is respectful, open, and just plain fun to be with. Last night, he expressed wanting to take it to another level and asked if I'd be interested in having him cook dinner for me at his house. I said I would be interested in that, however, it will be a little while before it could happen because I'll be traveling on business here and there for the next week and I have plans this weekend.

 

I know I'll be seeing him at the restaurant briefly in between. I'm thinking the next time we do meet up, I should open the conversation about dating goals. (I would consider sleeping with him -- I am attracted to him in that way).

 

The purpose of opening that conversation, of course, would be to see if we are on the same page overall. I am dating with the hopes of having a long term/exclusive relationship. I haven't met anyone else, that I've been interested in sleeping with. If he says he's not looking for a relationship, I can accept that. I probably would sleep with him anyway if it comes to that (he may not actually be planning for that -- I not going to assume that's why he's inviting me to his home. Not all men do that. It's expensive to go out all the time. I'll give him the benefit of the doubt and deal with it according to how I'm feeling at the time.

 

All I'm saying is I want to be clear about what happens afterward. If he says he's not looking for a relationship, I'll believe him. In other words, if we sleep together and he becomes distant or less interested, that's fine, I'll move on.

 

However, if he says he's at least hoping for more and stays in the picture, I'll have to tell the other man I'm moving on.

 

I am also thinking I might want to wait until we do meet at his house when we are alone and it's quiet. Or, should I just put off going to his house for a while longer? I would usually tell someone else not to go to a man's house unless you are ready to have that kind of a discussion. It's usually pretty clear to me early on "where" other men are going or what they are looking for when I date them. I ask questions that are not too obvious and they're responses tell the tale. However, with this guy, it's not clear yet.

 

I'm 55, very attractive, been on a ton of dates and not into playing games. I don't sleep with every man I date, and wouldn't until after we've spent enough time together to to know that I like the person and enjoy his company and if I am comfortable enough and want to, I will. I haven't slept with anyone since my fiance passed away - haven't wanted to either.

 

The dating pattern with either of these guys has not been typical or what I've experienced, so I'm feeling out of my element. I need some input from the "outside". I've probably answered my own questions by writing this all out, and not seeing the forest for the trees :) That's why we have these boards.

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I don't think I understand. If you're willing to sleep with him, and you'd do that regardless of whether or not he wants a committed relationship with you and you're ok with it either way, why even bring it up? Why not just let it happen and see where it goes?

 

You've also neglected to mention whether you're comfortable sleeping with both guys while you date them both.

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Ah, well since you are an older woman, you have a good understanding of who you are along with your needs, passions and dreams.

 

You are lucky to have two men, take time to allow for proper adjustment of your feelings and trust to build. Each gent will show his differences and similarities, so try not to place them in the same boat. As you may find one being easier to communicate with in a deeper level than the other. So expectations should be minimal to nothing, in order to allow you to distinguish each others connection in simple terms. To just go by pleasures in dating will make your view skewed one way or another. You may find one with better balance to allow more things to come than to be all at once and fizzle.

 

You are in the cat birds seat, so don't feel rushed, and enjoy what you have without feeling you need to compromise.

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I think it's time to choose. And if you want a long term relationship and the second guy says he isn't looking for one, I wouldn't sleep with him. You'll just confuse yourself and you'll hurt anyway through your own doing. That is, if you ware serious about finding love. If you just want to play and juggle, sure whatever. But again, if you want a relationship, it's time to become exclusive with either one or the other and clarify where you stand with each.

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I don't think I understand. If you're willing to sleep with him, and you'd do that regardless of whether or not he wants a committed relationship with you and you're ok with it either way, why even bring it up? Why not just let it happen and see where it goes?

 

You've also neglected to mention whether you're comfortable sleeping with both guys while you date them both.

 

mightycpa: That boils it down nicely. Thank you for the thoughtful, insightful response. As for sleeping with the first man, we are not at that point for sure. I do feel attracted to him in that way. But the "comfort" level would still be lacking even if it came to that point now. I would not be comfortable sleeping with two men. I prefer to sleep with one man until one or both of us decide it doesn't work.

 

The fact is though that at my age, I am established emotionally, have a balance life and am happy being single in general. I do not have to have an agenda for some one in my life anymore. I do, however, hope to have someone who is at least committed to me. So, far, guy 2 is creating the environment that makes me at least hope for that with him. There are never any guarantees. The real question here is, would he view my sleeping with him in a negative way. If he is looking for an exclusive/committed relationship and thinking he may want to go that way with me and I sleep with him, will that change it for him.

 

That is a very subjective question. Each person is different. The only way to know is to address it directly. Some men/women are ok with sleeping with someone outside of an established relationship. Some are not. I am OK with it (as long as there is some connection and not indiscriminate).

 

I guess it's just the double-edged sword. I can fall on the sword :) It won't kill me.

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You'll just confuse yourself
C'mon BIL, she was born before there were 50 States in the Union. She remembers where she was when Kennedy was killed, she watched as Walter Cronkite announced that astronauts landed on the moon, she may have even seen Earl Weaver lead the Baltimore Orioles to a win in the World Series. She remembers when Nixon resigned and she listened when Peter Frampton first asked if she feels like he feels. She's pretty clear that sex ain't love.

 

That's right, isn't it OP? You wouldn't still get your emotions involved just because you slept with him, would you?

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Ah, well since you are an older woman, you have a good understanding of who you are along with your needs, passions and dreams.

 

You are lucky to have two men, take time to allow for proper adjustment of your feelings and trust to build. Each gent will show his differences and similarities, so try not to place them in the same boat. As you may find one being easier to communicate with in a deeper level than the other. So expectations should be minimal to nothing, in order to allow you to distinguish each others connection in simple terms. To just go by pleasures in dating will make your view skewed one way or another. You may find one with better balance to allow more things to come than to be all at once and fizzle.

 

You are in the cat birds seat, so don't feel rushed, and enjoy what you have without feeling you need to compromise.

 

I am old enough to be able to do that for sure. I do have a dating goal which is to have a long-term, committed relationship, however, the process will be different with each man I date. That is the root of all the dating questions that come up. Everybody is different. I have a goal, but not an agenda. I do not have to work within the box anymore. I am certainly no longer a virgin and don't need to save it for the perfect man and a marriage goal. But, I do want it to be special. I have only slept with my ex husband and my fiance in my 55 years. It may really just be about inexperience with sleeping with someone new.

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C'mon BIL, she was born before there were 50 States in the Union. She remembers where she was when Kennedy was killed, she watched as Walter Cronkite announced that astronauts landed on the moon, she may have even seen Earl Weaver lead the Baltimore Orioles to a win in the World Series. She remembers when Nixon resigned and she listened when Peter Frampton first asked if she feels like he feels. She's pretty clear that sex ain't love.

 

That's right, isn't it OP? You wouldn't still get your emotions involved just because you slept with him, would you?

 

No, mightcpa, I wouldn't. I just want to know before I go. I heard on Conan O'Brien that a new study shows that some people don't get upset or emotional after a one night stand -- those people are called men :)

 

But, seriously, I don't think all men are so unemotional as to not experience some emotion when having sex. But, they are wired/maybe conditioned by society/parents, etc. to be able to remove themselves more easily from their emotions.

 

The fact is I am having emotions before I've slept with him. That is the hard part. I've also never considered having sex with anyone without having emotions before. I've never just jumped into bed with anyone.

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Well, you've been dating for 2 months. You sleeping with him at his point is not likely to change how he views you. It's not been 2 dates.

 

But if you sleep with him, I would not go on dates with the other one, and I would discuss exclusivity. I'm not sure I could sleep with someone and still go on dates with someone else if I'm looking for a relationship. That scenario is a FWB. It's just too complicated. I wouldn't be able to handle that. But maybe you can, since...what mightycpa said.

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That's funny. Well, yes, I hadn't read the 2 men in 55 years part yet.

 

If that's the case, then you're unusual for your time. Sex revolution and the 1980's and all that. You're probably not on the same playing field as these two men you're seeing.

 

But I still have my original confusion. Now you say your emotions are involved before sex. That would imply that whether you sleep with him or not, you'd be emotionally disappointed if he stopped seeing you, or if he used you. Throw in sex, and I don't see that ending well at all. You should probably take it a little slowly.

 

And back to that comment about men, one other thing they will do is lie to get sex. So if you verbally ask if he wants a relationship before you sleep with him, you might just get another answer after. For you, it is probably better to heed actions, not words.

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You two guys sound pretty cool, sensitive, mature guys. If I were dating you two, I may have a tough choice :) Thanks for your input. Very interesting conversation.

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That's funny. Well, yes, I hadn't read the 2 men in 55 years part yet.

 

If that's the case, then you're unusual for your time. Sex revolution and the 1980's and all that. You're probably not on the same playing field as these two men you're seeing.

 

But I still have my original confusion. Now you say your emotions are involved before sex. That would imply that whether you sleep with him or not, you'd be emotionally disappointed if he stopped seeing you, or if he used you. Throw in sex, and I don't see that ending well at all. You should probably take it a little slowly.

 

And back to that comment about men, one other thing they will do is lie to get sex. So if you verbally ask if he wants a relationship before you sleep with him, you might just get another answer after. For you, it is probably better to heed actions, not words.

 

You're right, except I always advocate looking at both words and actions. If actions are there but words are not, it could mean that he doesn't want to lie, there is a reason he's not saying what needs to be said. It needs to be said and if he lies, he needs to take responsibility for his lie later. If words are there and actions are not....don't need to explain what that means.

 

So I think it needs to be discussed and not implied and the multidating should stop after 7-8 dates or so and definitely after sleeping with one of them...in case you are a relationship seeker.

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That's funny. Well, yes, I hadn't read the 2 men in 55 years part yet.

 

If that's the case, then you're unusual for your time. Sex revolution and the 1980's and all that. You're probably not on the same playing field as these two men you're seeing.

 

But I still have my original confusion. Now you say your emotions are involved before sex. That would imply that whether you sleep with him or not, you'd be emotionally disappointed if he stopped seeing you, or if he used you. Throw in sex, and I don't see that ending well at all. You should probably take it a little slowly.

 

And back to that comment about men, one other thing they will do is lie to get sex. So if you verbally ask if he wants a relationship before you sleep with him, you might just get another answer after. For you, it is probably better to heed actions, not words.

 

Yes, men do lie. However, this man has been pretty direct and I know he doesn't appreciate lying from anyone else and I have seen him call someone out about lying. His character is not in question. What is in question, is where I am.

 

As for my pre-sex emotional state, I can keep them in check and it will be easier if I know/understand ahead of time. If I ask him, he will be direct. I will appreciate that and perhaps be even more comfortable with "just doing it". I can handle emotions . . . I went through a divorce and a death. What's left that's worse than that?

 

I was married for 30 years and engaged for two. Otherwise, I guess I may have become a more decadent woman for the times.

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You two guys sound pretty cool, sensitive, mature guys. If I were dating you two, I may have a tough choice :) Thanks for your input. Very interesting conversation.
How could I not like that? (PS, no, the choice would not be tough. No offense BA.)
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You're right, except I always advocate looking at both words and actions. If actions are there but words are not, it could mean that he doesn't want to lie, there is a reason he's not saying what needs to be said. It needs to be said and if he lies, he needs to take responsibility for his lie later. If words are there and actions are not....don't need to explain what that means.

 

So I think it needs to be discussed and not implied and the multidating should stop after 7-8 dates or so and definitely after sleeping with one of them...in case you are a relationship seeker.

 

His actions and words are in synch so far. I think if I just ask him, he will be honest. If he is being honest and says he's just looking for a casual/fun relationship that includes sex, I could be comfortable with that. I appreciate honesty. I can let it be what it is.

 

The hope/search for someone who is committed/exclusive will be a winding road. I was married for 30 years and engaged for two. So my "experience" with that road is limited. But, I can drive 55 :)

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Well, you've been dating for 2 months. You sleeping with him at his point is not likely to change how he views you. It's not been 2 dates.

 

But if you sleep with him, I would not go on dates with the other one, and I would discuss exclusivity. I'm not sure I could sleep with someone and still go on dates with someone else if I'm looking for a relationship. That scenario is a FWB. It's just too complicated. I wouldn't be able to handle that. But maybe you can, since...what mightycpa said.

 

BlueEyeL: That is the crux of this situation really. I have to decide whether to sleep with Guy 2 and let go of the other. But, the other way to go if Guy 2 is not looking for a relationship and just wants a casual/fun time of companionship and I am not in a relationship with anyone else, I can choose to do that. The fact is that unless and until I am committed to anyone, I am free and way over 21. I am not a virgin and don't really have to have an agenda at this point, although I have a goal. How that happens is going to be part of the journey.

 

I have been confronted with something that has maybe put me on the fence about what I am looking for, thus the confusion.

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It's time for you to make a decision and choose just one man, no matter what happens next.

 

On a different note, I want to congratulate you for your dating success at the age of 55. I'm over a decade younger, currently in a relationship and I'm telling myself that if this doesn't work, I don't want to continue dating if I reach 50. But I can see you're not doing too bad, good for you! :)

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BlueEyeL: That is the crux of this situation really. I have to decide whether to sleep with Guy 2 and let go of the other. But, the other way to go if Guy 2 is not looking for a relationship and just wants a casual/fun time of companionship and I am not in a relationship with anyone else, I can choose to do that. The fact is that unless and until I am committed to anyone, I am free and way over 21. I am not a virgin and don't really have to have an agenda at this point, although I have a goal. How that happens is going to be part of the journey.

 

I have been confronted with something that has maybe put me on the fence about what I am looking for, thus the confusion.

I understand. You have a goal. When we have a goal, we need to also have an "agenda" if you want to call it that way or a plan towards reaching that goal. If you are clear on the goal, you shouldn't let other side "objectives" (i.e. casual sex) derail you from the said goal. If you let yourself do that, fine, but your goal will be pushed aside by said actions.

 

So talk to the guy you want to sleep with, tell him you like him, you feel close to him but you tipically have sex in an exclusive relationship. Then ask "do you think we are there or need more time to know each other before that step?". Then listen to what he says and make a decision.

 

But it sounds to me that you already made your decision, you chose guy 2.

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It's time for you to make a decision and choose just one man, no matter what happens next.

 

On a different note, I want to congratulate you for your dating success at the age of 55. I'm over a decade younger, currently in a relationship and I'm telling myself that if this doesn't work, I don't want to continue dating if I reach 50. But I can see you're not doing too bad, good for you! :)

 

It's both fun and difficult. I happen to be on a little bit of a streak and maybe I'm just wanting to use it to my advantage in the sense of actually finding someone and exploring the options I have to their fullest.

 

Because of the "slowness" of guy 1 and the lack of opportunity to get really comfortable with him, I am now leaning toward guy 2 and letting the chips fall where they may. I'm going to be direct, get my answer, an accept what it is. That is how I'm feeling right now -- tomorrow may be a different story :) It's not really about rushing things (although at 55 there isn't a whole lotta room for wishy washiness either), it's about seizing the moment. Not to mention the possible dry spell that may follow . . .

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I am old enough to be able to do that for sure. I do have a dating goal which is to have a long-term, committed relationship, however, the process will be different with each man I date. That is the root of all the dating questions that come up. Everybody is different. I have a goal, but not an agenda. I do not have to work within the box anymore. I am certainly no longer a virgin and don't need to save it for the perfect man and a marriage goal. But, I do want it to be special. I have only slept with my ex husband and my fiance in my 55 years. It may really just be about inexperience with sleeping with someone new.

 

Ah, that is so with my LDR, she too knows her sexual self but is not over exposed to men in general. I think that is better for you in the long run. As you will find in dating, not all men are equal, just as women are. Being outside the box is always best, but when your younger you try to fit everything together neatly so to speak.

 

There is a lot to admire about a woman who is in your shoes, in that your not so tainted or should I say jaded by experiences and expectations. All a woman needs is to believe in herself and not sway to demands in dating. So many old ways of dating have been put aside because women know men don't have to be so gentlemanly to get what they want.

 

Though, I see similarities with you in respect you are finding freedom you never had, or admire from long ago. My LDR only had two younger men in her sexual experiences. So she is learning new tricks so to speak in seeing more than what she ever had.

 

You seem confident to know where things will go, just strikes me odd you make it seem like you need advice.

 

As my LDR says... go with the flow, and allow yourself to feel comfy all the way through. If you are not comfortable, then say so about it, and see how

the other responds. If they care for you truly, then they will accept and do what is best, either for you or for them. Just because you are older now, does not mean there is nothing left for you out there. There are a few good men that meet your needs, so don't limit yourself to find a particular age that matches you, go with the man who is mature as you mentally. I'm roughly 6 years younger than my LDR, and at times she thinks of me being younger by age and looks. But everything else is equal because she is young at heart and in body.

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Ah, that is so with my LDR, she too knows her sexual self but is not over exposed to men in general. I think that is better for you in the long run. As you will find in dating, not all men are equal, just as women are. Being outside the box is always best, but when your younger you try to fit everything together neatly so to speak.

 

There is a lot to admire about a woman who is in your shoes, in that your not so tainted or should I say jaded by experiences and expectations. All a woman needs is to believe in herself and not sway to demands in dating. So many old ways of dating have been put aside because women know men don't have to be so gentlemanly to get what they want.

 

Though, I see similarities with you in respect you are finding freedom you never had, or admire from long ago. My LDR only had two younger men in her sexual experiences. So she is learning new tricks so to speak in seeing more than what she ever had.

 

You seem confident to know where things will go, just strikes me odd you make it seem like you need advice.

 

As my LDR says... go with the flow, and allow yourself to feel comfy all the way through. If you are not comfortable, then say so about it, and see how

the other responds. If they care for you truly, then they will accept and do what is best, either for you or for them. Just because you are older now, does not mean there is nothing left for you out there. There are a few good men that meet your needs, so don't limit yourself to find a particular age that matches you, go with the man who is mature as you mentally. I'm roughly 6 years younger than my LDR, and at times she thinks of me being younger by age and looks. But everything else is equal because she is young at heart and in body.

 

It's not so much about advice as insight, clarity. I am "inexperienced" with seeing/being with different men. As I said above, I'm confronted with something that's taking me out of my element and questioning what it really is that I'm looking for now. I was thinking I want something more formal and at the same time realizing that I do have freedom and can try other dating "models", etc. I am on the fence I guess.

 

I said to BluEye that as of now I'm thinking I'm going to go with guy 2 and let the chips fall where they may. I don't have to stop seeing Guy 1. I just won't sleep with him until I know Guy 2 is out of the picture. I will be direct with him and he will be direct with me. If nothing else, it will just be a new experience with a little added fun :) I'm kinda thinking its about Schroedinger's cat -- you don't know until you open the box.

 

I also said to BluEye that I'm free and way over 21. I have options and not a lot of fear!

 

One other thing, if I go to guy 2's house and it doesn't come down to sex . . . guy 2 will be Guy #1.

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One other element here that I am being cognizant of is that one or both of these men may have some investment emotionally. If I don't think about this as a two way street, I am not being fair.

 

And one thing I neglected to mention here and just now remembered and that I only became aware of two days ago, is that these two men know each other. I heard this in passing conversation with someone else. That person was talking about two guys relative to something. I just now put it together. They are not close friends, but acquaintances. I owe nothing to either of them, except Respect.

 

I gotta choose . . . subconsciousness is a powerful thing. I wasn't tuned in to this and is the reason I couldn't see this clearly and felt the need to post. Oh my. It's ok, I've decided what I'm going to do though I didn't realize why :)

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One other element here that I am being cognizant of is that one or both of these men may have some investment emotionally. If I don't think about this as a two way street, I am not being fair.

 

And one thing I neglected to mention here and just now remembered and that I only became aware of two days ago, is that these two men know each other. I heard this in passing conversation with someone else. That person was talking about two guys relative to something. I just now put it together. They are not close friends, but acquaintances. I owe nothing to either of them, except Respect.

 

I gotta choose . . . subconsciousness is a powerful thing. I wasn't tuned in to this and is the reason I couldn't see this clearly and felt the need to post. Oh my. It's ok, I've decided what I'm going to do though I didn't realize why :)

 

Well, that is to be expected... I have that way in communication with my LDR. I see things differently and in a round about way, I allow for the other to think about things, rather than tell them how I feel about it. As they have the answer before them, just need a wee push in a way.

 

I think I drive people up the wall with how I just bring up thoughts to the issue at hand. Not being analytical with the processes. Being simplistic to the obvious is how I see things. Some times the obvious is not so clear until it is brought full circle.

 

Only if I was this way to myself long ago... as I would have found answers that were never seen before me.

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If you sleep with no 2, the right thing to do would be to let no 1 go and wish him well. Don't string him along. You can't have your cake and eat it too. Especially since they know each other.

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If you sleep with no 2, the right thing to do would be to let no 1 go and wish him well. Don't string him along. You can't have your cake and eat it too. Especially since they know each other.

 

Yep, that's what I'm going to do. I knew there was something about all this that I couldn't put my finger on. I had an epiphany so to speak. It's funny how the mind works. Something so simple that I heard in passing and filed away came to the surface.

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