Dating advice?

nllswing

Member
I’d like to hear the thoughts of more experienced poly folks about what I should do in my situation. I am hoping for an interesting discussion.

Here is the problem:

After figuring out that online dating borders on “lost cause” for me as a married guy in an open relationship, I stumbled upon a different opportunity: I have a vanilla interest and found a place, not far from where I live, where people with that interest gather. Let’s call that place “the club.” The older folks outnumber those that are my age and the women outnumber the men, sometimes by large margin. Unlike a dating site there people can just pass on, the place here makes us know each other and warm up. There is a whole bunch of people I’d love to be “friends or more” with. So far so good :)

There is one woman in whom I am seriously interested. She is beautiful and it is clear that she knows it by the way how she dresses up. She is very intelligent, comfortable with who she is, and seems quite happy with her life. Her husband has passed away a long time ago and nothing suggests that she is in a relationship. I am in my late 30s and she is at least 60.

We talked a few time in the club about the vanilla hobby and exchanged phone numbers. We spoke a few times on the phone briefly, arranging to meet independently regarding the vanilla activity. Ten days ago, on the weekend, after some back and forth (each of us calling the other), we met outside once and had good time for a couple of hours, which ended with a nice general talk.

So far this is the farthest we went. We planned that each of us go on Tuesday as usual for an event at the club. Few hours before the start she called to say that she had an eye procedure, did not feel comfortable, and would skip the event. “I though I should let you know” she said. It was an unpleasant surprise, but I kept hoping that will meet her later. In any case, I was hoping that she would show up today as well, but she did not. We haven spoken since; I called once and nobody answered.

I wander about a few things. On one hand, being almost 30 years my senior, she might not even think that I could be interested in her. On the other hand, I suspect that a woman with her brains would sense from miles if someone is into her. I don’t know which factor prevails.

I am not sure how to proceed here
. Normally, I will just try to call, pretend to be calm, and either ask her to meet our or plan something for the vanilla club.

I haven’t told her yet that I am married and in open relationship. I plan to do this once there is any indication of mutual romantic interest. The reason is that I don’t want to scare her away before giving her a chance to know me better. Athena (my wife on this board) and I now live in two places during the week and see each almost as rarely as every other weekend. Thus, we are not in a poly community where everyone knows us as a couple.

Any thoughts?
 
This is a tough situation, and I think others have had a similar dilemma.

Do I tell them that I am poly before there is romantic interest and run the risk of scaring them away or do I find out if there is an interest first.

The problem with waiting is that she may start feeling more and more invested in your relationship, assuming that you are single - when she finds out that you are married and poly she may well feel lied to, even if it is a lie by omission.

The idea that somehow an interest in you would trump an aversion to poly and that this omission of something that fundamental wouldn't be a show-stopper for someone seems problematic to me, especially when poly is supposed to be based on the concept of openness and honesty. What message does it give when the first exposure to poly is that you felt it necessary to hide a significant and relevant aspect from her?

I believe that if poly is a show-stopper, then it's going to be that no matter how well she knows you. So I feel that it's best that you bring it up in casual conversation and have the discussion before turning the focus of your friendship to more romantic topics.
 
Hi there. First of all, I keep chuckling over your use of the terms "vanilla interest," "vanilla hobby," etc. I wouldn't have automatically thought that any hobby, interest, or club a person joined would be kink-related, so to keep mentioning that it's "vanilla," as if to let us know it's NOT kinky, kind of cracks me up! And makes me even more curious, ha-ha!

So, on to your dilemma - I think I would agree that you don't need to bring up poly before knowing if there is any interest on her part. I never see the point in doing so myself, unless someone specifically asks me what my relationship status is. Personally, I feel that if it's a social event not organized specifically for dating or meeting prospects for dates, and you meet someone there, it's an arrogant assumption to tell them right away that one is poly. It comes off like you're assuming they want you, but they'd be like, "Okay, who asked you?" I mean, if you weren't poly in this situation, would you jump at the chance to hit everyone over the head with the fact that you're married when all you're doing is getting together to share an interest in a hobby? Methinks not. At this point, you're simply developing a friendship, you have an attraction to her, and you're not sure if she is aware of that or has mutual interest, so how you've handled it all sounds okay to me so far. I would probably try to find a way to bring it up the next time you see her outside of the group's activities, if she expresses an interest or if you feel like there's enough time and a relaxed enough atmosphere to talk about relationship stuff.

So, are you saying that there were two Tuesdays in a row that she did not attend the club activities where you would normally see her? If I were you I would wait until a few days before the next regularly scheduled meeting and call her to check in and ask her how she's doing. Keep it friendly and relaxed. See if she needs anything, after having that procedure, and offer to help if you feel that's appropriate. Then I would just say something like, "I just wanted you to know I was thinking of you and hope to see you soon." That should be a good opening for her if she wants to converse some more, make a date to meet, or ask you anything. Does that sound reasonable to you?
 
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thank you

Thank you NYCindie,

I was hoping that someone as experienced as you would answer. I know that the stuff about the "vanilla club" sounds odd, but I don't want to name the activity because it is not that hard to connect the dots.

What you suggest is quite reasonable, and what scares me is that things went so well initially that I am a bit afraid to mess them up.

Yes, she did not show up two time in a row but as far as I gather, she has plenty of things to do in her life and the club is not her only activity. I have been going there over the last couple of months and she was there no more than four times total.


CielDuMatin, thank you for the comment. I think I will keep the poly stuff out for now because I suspect it is alien to her. I agree with your comment about making an "omission" but I want to reach a stage where she would at least listen and let me explain myself before making her decision.
 
I definitely appreciate your dilemma, and I respect your decision.

The only thing I would counsel is to not let her get too invested in you before you tell her. If she is someone you care about, you wouldn't want to hurt her, would you?
 
I definitely appreciate your dilemma, and I respect your decision.

The only thing I would counsel is to not let her get too invested in you before you tell her. If she is someone you care about, you wouldn't want to hurt her, would you?


No, I don't want to hurt her, but as I said, I will let her know once there is an indication of mutual romantic interest. In other words, in the moment I see that she is interested. She is at a very different place/stage in life and there are a few bridges to cross first. This is not like tricking a young girl at the county fair, where anything other than marriage is a deceit. :)
 
An update (probably final)

It is time for an update:

After she did not show up twice, I called her last week. We had a nice short chat and made a plan to visit the club on what was then "the next Tuesday" which was yesterday. Yesterday we had a great time at the club, then walked to her car and made plan to meet today.

Today me met outside of the club as planned, had a good time and finished with a very nice conversation over drinks. As the time to get up was approaching, I asked her if she had any plans for the second weekend from now because this would be the time when I would have a weekend off here.

She asked: is it about [the activity]?
I said: Yes, and also to spend some time together, to talk.
She then said: But why do you want to do that?
I answered: Because I like your company.
Here, she continued with "but I am much older than you" and after I answered with "yes, I know" she explained that she has a full life and that she was reached to a point where she is not interested in romantic activities.
Then she said something of the sort of "I am not sure if this has actually crossed your mind, but I want to make sure."

Then we got up, picked our stuff from the coat check, walker to her car just a few steps away and amicably parted.


I AM SO SAD! It hurts so much to be rejected!
I know that the chances were slim, but gosh, she is really a woman I wanted to be with. She is smart, very beautiful, and very sophisticated. It hurts so, so much to be rejected. I had a lot of rejection when I was younger, and not that much since I have been married :) (now too much dating), but gosh, it is painful. And the sad part is that I will continue seeing her at the club and I don't want to stop going.

So, here it ends. While she mentioned age first, and she said that she is in general not interested in dating, I know that if she liked me romantically, she would have gone for it because she knows what she wants and how to get it. I hate it when love hurts so much!

Now I am thinking: "man, if you are not good even for a toyboy, you are really good for nothing."
 
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She then said: But why do you want to do that?
I answered: Because I like your company.
Here, she continued with "but I am much older than you" and after I answered with "yes, I know" she explained that she has a full life and that she was reached to a point where she is not interested in romantic activities.
Then she said something of the sort of "I am not sure if this has actually crossed your mind, but I want to make sure."

Wow, what an opportunity! Did you tell her, "Yes, it has crossed my mind many times." Or did you just leave it at that? Because I think that was the perfect chance to let her know about your non-monogamous marriage, your romantic interest in her, and (I hope) that she still has your friendship. She might feel that she has no room for romance in her life right now simply because she hasn't seen the possibility for it. Why not give her something to consider while you still invest in the friendship. With all your cards on the table, she might be moved to do something out of her comfort zone, or out of character for her, after some thinking about it.

While she mentioned age first, and she said that she is in general not interested in dating, I know that if she liked me romantically, she would have gone for it because she knows what she wants and how to get it. I hate it when love hurts so much!

Now I am thinking: "man, if you are not good even for a toyboy, you are really good for nothing."

Don't think it is you, beating yourself up is so unkind! Age can be huge for some people. The other day a guy who is 30 years younger than me contacted me on OKC and I. just. couldn't. Some things are too hard to get past... initially.
 
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Well, NYCindie, I did not think to answer her with the quote you wrote, but from her tone I gathered that it was more like "I suspect you are trying to date me and I am not interested." And one more thing: her "I am not sure if this has actually crossed your mind, but I want to make sure" was not a question. I was a preamble to her continuing with her being not interested.


In other parts of the conversation, I could have explained more about my marriage but I just thought that it was too early and the things was moving so smoothly that I did not want to disturb them.
 
While she might have made a different decision if she knew the situation (for instance, maybe she doesn't want to be your girlfriend because she would want you to have the opportunity to have someone your age. A lot of people avoid dating younger people because they feel they would be taking something away from them. Learning you were married and poly could have made a difference) I would still go with leaving things be, at this stage.

She went out of her way to let you know she wasn't interested. I think insisting would easily be seen as disrespectful. You can probably still hang out at the club at least, and maybe more, but in a friendly way only. If the topic of your wife and/or your polyamory comes up, then sure, but don't force it.

I think that if you got the feeling that she wasn't interested, her exact phrasing might not matter. Sometimes people try to let you down nicely.

I am biased, because I have had a bad experience with "insisting". For instance, I asked a teacher out when I was in university, after the year ended. Because I was still going to attend the university (not with him as a teacher) he said, he couldn't date me.
I didn't think to say anything at the time. And if I had wanted to say anything at all, I should have done it right then. Instead, I went to him again later and pointed out that the problem was easy to solve as this university was hardly the only one I could attend, nor the closest to where I lived.
Long story short, while we had previously ended it on friendly term, he was really put-off by the fact I insisted and became upset with me, and seemed to feel worried by me (like I was some kind of stalker).
It was pretty hurtful, and I'm mentioning it here so that you know what my own experience is and how it is heavily influencing my advice. This instance wasn't the only time it happened (my insisting and ruining things), but it seemed to be the most relevant one to your situation.

If I could go back, I would still ask him out, because I think it's important to know even if the answer is no. But I wouldn't insist after being rejected, because I only made things worse.

I'm really sorry about how bad you feel. I understand you really like her. I hope you will be able to see her more and maintain a friendly relationship.
 
She went out of her way to let you know she wasn't interested. I think insisting would easily be seen as disrespectful.

Some things apply whether we're talking monogamy or polyamory. This is one of them.

I am biased, because I have had a bad experience with "insisting". For instance, I asked a teacher out when I was in university, after the year ended. Because I was still going to attend the university (not with him as a teacher) he said, he couldn't date me.
I didn't think to say anything at the time. And if I had wanted to say anything at all, I should have done it right then. Instead, I went to him again later and pointed out that the problem was easy to solve as this university was hardly the only one I could attend, nor the closest to where I lived.
Long story short, while we had previously ended it on friendly term, he was really put-off by the fact I insisted and became upset with me, and seemed to feel worried by me (like I was some kind of stalker).
It was pretty hurtful, and I'm mentioning it here so that you know what my own experience is and how it is heavily influencing my advice. This instance wasn't the only time it happened (my insisting and ruining things), but it seemed to be the most relevant one to your situation.

Are you me? I mean, damn, that was my 2007. Much love to you for getting through it.

There is a serious "no means maybe" problem, isn't there? Romance novels and romantic comedies tell us this is a fine strategy to employ, and then we employ it without realising we're not characters. We're humans. And humans tend to get fed up with that kind of insistence in a hurry. I've insisted; I've been on the receiving end of insistence; it never ended well. No has to start meaning no, and so these days I behave in ways that are consistent with that philosophy.
 
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I never advised that you insist on anything, I hope you know.

I just thought you had an opportunity for a conversation, which might allow her to get a bigger picture of who you are and what exactly you had in mind. And give her something to think about. But NOT by being insistent in any way!

The good thing is you can still develop the friendship. And friendship is no small thing, right?
 
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Thank you for all the new input. After reading NYCindie's post from a few days ago, it occurred to me that the woman I am interested in has a very rich and full life and values her freedom and independence. It would be very hard to make her consider becoming responsible about someone, as it is expected in traditional mono relationships.

After the initial pain, I felt not as bad because I am not lonely (I have Athena). In addition, I could still keep the friendship with her and could let her know me better if she agrees to keep seeing each other in relation to the club activity. The latter I may suggest depending on how things go.

I agree that insistence is a lost cause. I did this for a very long time when I was in my teens. It did not work.

Currently, the situation is as follows: there is a likelihood that we will still be doing some of the club activity together: today I got a few emails from her regarding something in the club, inquiring if I will be participating.
 
UPDATE - any thoughts?

So, the story continues as follows:

We continued meeting at the hobby club and sometimes outside in relationship with the hobby (what I previously was calling "vanilla activity" - it is a plain non-sexual hobby). In the last few weeks we have been skipping the club most of the time and have been meeting at her alumni club, which is a convenient place. Each time when we'd meet, we'd have a nice conversation for an hour or so, and then we'd get to work. These conversations are my favorite time and I let her, bit by bit, know more about me. I have been also learning quite a bit about her and her interesting life :)

Today I brought the topic of open relationships. Until now, she knew that my wife and I had "an arrangement." While she wasn't shocked at all, she said that she tried once to have a casual relationship and it did not work well for her. Then she mentioned something like "luckily, I don't have to worry about relationships any more." I told her some of the benefits an open relationship can offer and what my wife and I have agreed upon, and she tole me "I wish you luck." Also she told me that last year she had something with a guy in his 40s, so age gap is not such a big issue for her. There is something else.

After the dinner talk we did some hobby work and friendly parted with the understanding to meet next Tuesday at the hobby club because we haven't been there in a while.


I don't know what to do. I am in love, she is gorgeous, and it hurts me to come home after our meeting be start thinking about why aren't we lovers. Things have been going fine, except that we may be stuck at the "activity friends" area, and this is not acceptable for me. First, it hurts me because I really want us to be more and second, spending two evenings a week to be a "friend" is too much time for me.

I often imagine telling her "listen, it has all been fine but I can't keep going like this" but on the other hand, I don't want to break things up just yet.
 
I don't know what to do. I am in love, she is gorgeous, and it hurts me to come home after our meeting be start thinking about why aren't we lovers. Things have been going fine, except that we may be stuck at the "activity friends" area, and this is not acceptable for me. First, it hurts me because I really want us to be more and second, spending two evenings a week to be a "friend" is too much time for me.

I often imagine telling her "listen, it has all been fine but I can't keep going like this" but on the other hand, I don't want to break things up just yet.

Oh dear. Nllswing, I urge you not to let your attraction and desire for her cloud your judgment! Who among us can ever not benefit from a friendship?

She has given you a lot already, hasn't she? You enjoy her company, you are getting close - don't discount her place in your life just because she doesn't want to be involved with you in that way at this point in time. You don't want to blow it all and hurt her by taking yourself out of her life just because you wish it was a romance instead of a friendship. I say, invest in the friendship and let it deepen. Embrace all the feelings you have about her, and just let yourself feel them. I have always believed that we can benefit and learn a great deal from not taking action when we most want to. There is something to be said for allowing oneself to experience the love/lust/desire, etc., without giving in to the urge to do something about it. For now, let yourself get all hot over her and then, when you get home, direct that passionate energy to your wife.

I think that you would be cutting your nose off to spite your face, if you push it to be something more. It really hasn't been that long, try not to get so impatient. The desire and lust you feel for her will either eventually burn itself out, or she may come around and consider something more - but what if it takes a year or two for that to happen? Would you toss away a good friendship because you can't have your way now? Or you can simply enjoy having such a wonderfully delicious crush in your life. My goodness, not every temptation or fantasy needs to or should be be acted upon! I don't see why you cannot pursue a romance with someone else and still have your friendship and hobby once or twice a week with her. Count your blessings. It sounds too good to let go of, just the way it is right now!
 
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Thank you for the thoughtful advice NYCindie :)

I have been thinking about what to write here, but almost nothing would make sense, so I'd leave it as it is. Each thought you present of quite true, but when I think about the whole picture, something feels odd. In any way, I will hang on and will see what happens.

By the way, I have been seeing somebody else in the last couple of months, and we are a bit more that hobby friends, but this is a separate story.
 
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