I thought I’d be happy/relieved if she found someone; turns out I’m sad

[Batya33]

5 hours ago, NighttimeNightmare said:

Ya that doesn’t mean that I “think that people who are married were in general desperate to find a partner otherwise they would be single” That’s a really weird leap. I was making two separate comments about myself and how I operate in direct relation to some of her own world views 

 

I don't think it's a weird leap at all -you've expressed some rather atypical/strong opinions about your approach to relationships.

Also I would not assume at all she is expressing her "world views" -she is expressing her opinion in a specific context and since you two are not romantically involved or a couple etc she isn't necessarily lying but may be expressing what she thinks she should in the moment/feels in the moment.  

[Batya33]

5 hours ago, NighttimeNightmare said:

And batya please don’t jump in with your suspicions that she’s some “mega sexual flirt” who feeds off of this. I understand you think this but it’s not helpful 

I'll ask you to please stop targeting me -I honestly had no idea what you were referring to and that is your description not mine.  Both of you enjoy using sexual innuendoes, dancing around the whole attraction thing and she seems to enjoy that sort of attention. And you enjoy giving her sexual attention.  As far as the man - obviously there are people who are going to try to interact with her -she's an attractive single woman at a party - it's normal and it's fine.  If she disliked it she had many choices - keep her distance, tell him politely to keep his distance, etc.  She's a grown up.  

But I wasn't going to respond to your example in the least -the whole thing sounds like a big nothing to me and only becomes a something because of your choice so far not to have a conversation with her about your intentions towards and feelings about her - that choice increases the chances of this sort of communication issue between the 2 of you IMHO.

[Batya33]

4 hours ago, rainbowsandroses said:

NN, have you thought about waiting for the right opportunity and simply kissing her?  On lips in a romantic way?

I have to think spending so much intimate time together, that opportunity was there many times. 

Not forcing yourself, it's gotta be natural.  You're spending NYE together?  Perfect opportunity

An anecdote - I was "friends" with my first serious boyfriend before we got romantically involved.  Very similar to your sitch. 

One night we were at a club, the vibe was great, we were drinking wine, and he looked at me very tenderly and kissed me.

I kissed him back and he said "I've been wanting to do that for a whole year"!

We dated/in a relationship for four years after that night.  

Anyway, my point is, I don't think it's necessary to 'spill your feels', just move close into her and kiss her, naturally. 

However she responds, THAT is your answer. 

What do you think? 

 

 

Or ask her out on a proper date planned in advance and make it clear it is a date.

[boltnrun]

Have you had any physical contact other than a hug hello or goodbye or incidental contact (TV remote, putting your hand on her back when she's walking ahead of you or past you)?  If not, I would not advise you just swoop in and kiss her.

[Wiseman2]

5 hours ago, NighttimeNightmare said:

 I think it’s beneficial for us both that we have a discussion about what this really is between us. I don’t want either of us to get hurt when new people come into the picture 

Ask if you can kiss her on New Year's Eve. It's kind of traditional.  What's the big deal? It's a lot better than weird remarks about masturbating to pics of her.

Not sure what that was about. But treating her with respect and like a NYE date, asking for a kiss at midnight seems like a better way to go. 

You're "allowed" to express yourself as much as you want. Unfortunately you seem to choose to blame her for all that stuff in your head and your own reticence. But then blurt out the weirdest sexual remarks? That's not on her either.

Act like a gentleman on New Year's. See how she responds to something as simple as a kiss at midnight. 

[NighttimeNightmare]

36 minutes ago, boltnrun said:

Have you had any physical contact other than a hug hello or goodbye or incidental contact (TV remote, putting your hand on her back when she's walking ahead of you or past you)?  If not, I would not advise you just swoop in and kiss her.

I don’t think so, like what? I mean she’s rubbed on my arm before, the way she did that seemed sensual. But nothing beyond that and how she touches my inner thigh to communicate with me when we sit next to one another in public, but that isn’t sensual. I mean if we had some sort of “heavy petting” at some point I wouldn’t be wondering if she was into me. So there’s been nothing major, just little things here and there 

[boltnrun]

4 minutes ago, NighttimeNightmare said:

I don’t think so, like what? I mean she’s rubbed on my arm before, the way she did that seemed sensual. But nothing beyond that and how she touches my inner thigh to communicate with me when we sit next to one another in public, but that isn’t sensual. I mean if we had some sort of “heavy petting” at some point I wouldn’t be wondering if she was into me. So there’s been nothing major, just little things here and there 

I wasn't referring to "heavy petting" which of course would at least indicate sexual attraction and interest.  I mean, do you sit with your arm around her while watching a film together?  Do you hold hands while walking?  Does she kiss you on the cheek goodnight?  

[NighttimeNightmare]

33 minutes ago, Wiseman2 said:

Unfortunately you seem to choose to blame her for all that stuff in your head and your own reticence

I really don’t feel like I blame her. I’m well aware these are all my own struggles that she has very little to do with, if at all.   I think people are more or less mirrors of ourselves in many ways. 
 

Am I frustrated, sure. Do I wish she would be the one to make a move if she’s interested. Yea.  But I don’t blame her for my own predicament and I don’t think the burden is on her. 

35 minutes ago, Wiseman2 said:

Ask if you can kiss her on New Year's Eve. It's kind of traditional.  What's the big deal? It's a lot better than weird remarks about masturbating to pics of her.

True.  I see the difference/contrast there 

[NighttimeNightmare]

1 minute ago, boltnrun said:

I mean, do you sit with your arm around her while watching a film together?  Do you hold hands while walking?  Does she kiss you on the cheek goodnight?  

Oh. Nope. I stop myself from touching her because idk what she’s ok with.  The other evening did seem like we were deliberately sort of touching one another’s hand while sharing a cocktail. But once again, I couldn’t know “for sure” so I didn’t make a move to actually try to hold her hand.  I know some on this forum have expressed my being over logical is not helpful, but I mean, that’s how my mind worked that night. 
 

The closest we got to a kiss was when she blew me one the other night at her friends dinner 

[rainbowsandroses]

1 hour ago, Batya33 said:

Or ask her out on a proper date planned in advance and make it clear it is a date.

Thanks but I like the kiss idea better which is why I suggested it to NN. 

Had my ex chosen to ask me on a 'proper' date and made clear it was a 'date' after being friends for a year, I would have felt extremely awkward and pressured.

I mean in this case, where NN and this woman spend time going out and doing date-like activities, what exactly is a "proper" date?  That just sounds too formal and planned, imo. 

Unnatural given their relationship in its current state.

By my ex simply kissing me at the right time, it all felt very natural and organic. 

Nothing forced, no suddenly planting one on her, that's not what I'm referring to at all. 

Honestly I do not get why this is a big deal. 

On NYE when the clock strikes midnight and the vibe is right, lean in, look at her tenderly, and kiss her.  Her response will tell you everything you need to know.

I'm not a fan of a man asking if he can kiss me, but NN if you're more comfortable with that, do that.

JMO.

 

[boltnrun]

In that case I think swooping in and planting a kiss on her suddenly isn't a great idea.

I do think the previous suggestion (to ask if you can kiss her at midnight on New Year's Eve) is a good one. See if it turns into multiple kisses. 

[NighttimeNightmare]

29 minutes ago, rainbowsandroses said:

Had my ex chosen to ask me on a 'proper' date and made clear it was a 'date' after being friends for a year, I would have felt extremely awkward and pressured.

I mean in this case, where NN and this woman spend time going out and doing date-like activities, what exactly is a "proper" date?  That just sounds too formal and planned, imo. 

Unnatural given their relationship in its current state.

I agree that at this point it’s way too late to ask her on a date. I know we aren’t dating but we basically are going on what resembles dates and have emotionally moved beyond that in a natural progression. I feel like months ago I could have asked her on a formal date, and used that to get to know her with intention, but it seems redundant and even elementary now.  I mean, we dressed up and went out to dinner last night, talked for hours, night before cooked at her place, talked for hours. I feel that to say “would u like to go on a date with me?” strange. It doesn’t prompt a situation that’s any different than what we are already doing. If anything I think it once again drums up the question of “what are we doing?” Because I can’t find differentiation between what she and I are doing, and what a couple on a date is doing 

40 minutes ago, rainbowsandroses said:

By my ex simply kissing me at the right time, it all felt very natural and organic. 

Nothing forced, no suddenly planting one on her, that's not what I'm referring to at all. 

I understand the nuances in what you’re getting at here. There is a natural vibe and progression I have going on with this woman and it’s certainly gotten to the point where I’m naturally feeling like we might be able to hold hands, or kiss.  It would need to be at the right time with the right vibe. That has happened a few times now but like I said, I wasn’t 100% certain so I backed off. 
 

but I can say she’s changing… like becoming more opened with me as the weeks go on. The other night I was laying on the bed and she was showing me her winter wardrobe and asking what I thought of certain outfits on her. Told her which colors I really liked on her.  A week or two ago when I was yapping to her about something she sat there smiling at me and had a certain look, I’d never seen her look at me that way before. It’s moments like those where I do feel I could have done it.  But it’s also in those moments she’ll start making comments about our age gap. 
 

I really do think she sometimes gets into wanting more with me and then pulls back. I think it’s almost time for me to seize one of the moments and get this all over with. 

[Wiseman2]

Ok. Here's the "logical" answer. At midnight 12.31.2023. 🎊 ask if you can kiss 💋 her for New Year's 🥂. Happy New Year!

[rainbowsandroses]

NN, have you read any of the articles posted in this section about the attraction and dynamic between a younger man and a much older woman? 

"I just read this one, super interesting!

"Can a Younger Man Find an Older Woman Attractive?"

Also, what is her relationship history?  Has she ever been married? Long term committed relationships?

With the little you've shared, she seems sketchy about commitment, which may be why she finds you so appealing since you're not pressing her for one?

I dunno, just some thoughts. 

This is kinda exciting though isn't it?  I'm excited for you, I hope it works out, keep us posted. 

[NighttimeNightmare]

37 minutes ago, rainbowsandroses said:

Also, what is her relationship history?  Has she ever been married? Long term committed relationships?

She was married once when she was my age. Caught him cheating and divorced him.   She’s told me she’s dated on and off since then and had more or less bad experiences. Just one guy she said she had really great chemistry with, years back, but turned out he had a wife at home; she feels a lot of guilt about this.  More recently (I’m talking within 10 years) she said she had met someone online and they had good chemistry on the phone but not in person. Another one changed when they made it official and she felt like he just wanted her for sex whereas she wants an emotional connection. Found photographs of him and a woman he had in another state, said she took a flight out of there and left.  Last guy died of cancer.   She says it was more or less who she was dating I guess, pilots. That’s who she was around all of the time, so. She said she realized the pilots all had women in different states and countries so she decided to never be involved with one again.  She said people out of the industry struggled with the fact she was gone all of the time, which made the relationships difficult, it was difficult to see people consistently and they couldn’t handle it. 
 

When we do have discussions about it she basically says to me “if someone has all of these bad experiences, it’s stupid to do it again. You say I just see the negative in everything but the negatives are there, they happened to me, so why would I subject myself to this again?” Which I get and tend to agree with save for the fact not everyone is destructive.  

then she will say to me that even I think most peoples relationships are dysfunctional. And I do. But not every person out there is. 
 

last we had this convo was when she said “so I’m supposed to just open myself up and see what happens and end up hurt”. I was like “if you open yourself up to someone, you step back when red flags come up. You have control over it. You don’t blindly believe someone’s words “

Then I go into my spiel about how “you know how I feel about this. I look for a connection and I let that develop. I like to really get to know someone. When you’ve got the connection you have the friendship and trust and you know how the person behaves when they’re happy, sad, angry, etc.  I have to get to know someone, but that’s just me” 

This was the convo where I told her I used to be abusive to my partners and had to learn how to communicate and to react with kindness and generosity during conflict. Told her I still struggle with b&w thinking and such, but I don’t feel I’m abusive anymore 

 

50 minutes ago, rainbowsandroses said:

With the little you've shared, she seems sketchy about commitment, which may be why she finds you so appealing since you're not pressing her for one?

Probably. If anything I think it’s made it easy for a genuine friendship to develop. Because I got to know her for her, not because I had an agenda to sleep with her 
 

But likewise, I’ve always enjoyed that she wasn’t pestering me for a relationship or that she was someone who constantly was trying to sleep with me. 
 

but now, obviously, I’d like some of those things 

 

 

this doesn’t seem to be an 100% commitment fear for her either though. It also seems to be an annoyance with people saying she has to be in a relationship or she’s defective, and pressuring her into one 

[NighttimeNightmare]

Well, sh*t, the New Year’s Eve thing is off… sort of, maybe.   She invited me as her guest to a party and the host came down with Covid. I could invite her to the party I was invited to, or maybe I can get creative and come up with something we do alone. But I’m also thinking she might end up at another friends house. Didn’t really discuss it with her cause she was on the phone so.. TBD 

[Batya33]

11 hours ago, rainbowsandroses said:

Had my ex chosen to ask me on a 'proper' date and made clear it was a 'date' after being friends for a year, I would have felt extremely awkward and pressured.

To each her own.  I was friends with a man for 1.5 years.  During part of that time I had a bf.  He was my friend's older brother - and every few months he'd call to say hi and talk about a specific interest we had in common. 

Then bf and I broke up. I'd never looked at this man as anything other than platonic friend/friend's older brother.  I invited him to a large group event related to our common interest- as a friend - literally to come along not as my date.  He said to be honest I'm just not interested in the event but would you like to go out for sushi on Sunday.  I didn't know if it was a date and we'd never gone out to dinner before alone.  I went. It was somewhat obvious it was a date.  Then he asked if I'd see a movie the next week and referred to it as a date.  We did kiss after the dinner but by then I realized it was a date. Had he made a pass at me I'd have felt taken aback and like he just wanted to hook up with me -he was a slightly reformed player so that was part of it.

[Wiseman2]

5 hours ago, NighttimeNightmare said:

. I could invite her to the party I was invited to, or maybe I can get creative and come up with something we do alone. 

Yes, invite her to the party. What's wrong with that? It's a win-win situation. 

[Kwothe28]

6 hours ago, NighttimeNightmare said:

I could invite her to the party I was invited to, or maybe I can get creative and come up with something we do alone.

What would she enjoy more? Does she likes being around people or is more "homebody"?

If she likes to party and not spend New Year at home, go for a party. Even if you try something, you can do it there. 

[rainbowsandroses]

14 hours ago, NighttimeNightmare said:

I understand the nuances in what you’re getting at here. There is a natural vibe and progression I have going on with this woman and it’s certainly gotten to the point where I’m naturally feeling like we might be able to hold hands, or kiss.  It would need to be at the right time with the right vibe. That has happened a few times now but like I said, I wasn’t 100% certain so I backed off. 

^^Thank you NN for understanding where I was coming from about the kiss idea, and I wholeheartedly agree about the nuances. 

Every friendship /situationship/ relationship is different.

And under different circumstances and a different type of friendship from what you have now where you're essentially going on "dates" anyway, asking her on a proper date may have been the better idea.  

I'm sorry the NYE party was cancelled and agree with others that it would a nice gesture to invite her to your party or plan something entirely different.

Good luck!  My new guy and I are off to the mountains for the weekend so hope y'all have a great time whatever you do.  

Make it count and Happy New Year! 

 

[NighttimeNightmare]

Spent the day with her again. We went for a 6 mile hike then went back to her place and we made dinner. Had a really interesting conversation 

I don’t remember how this came up, but she brought it up. Essentially the gist of the conversation was that she said my attempts at being polite and courteous are coming across as a lack of interest. She said she never knows what it is that I want, because I don’t ever tell her. She asked if that had to do with some people in my past.  I told her I’ve got some past issues for sure, going back to my childhood. I said as a child I learned to shutdown my own needs because it was easier, so a coping mechanism was for me to become passive In some ways and leave it all up to the other person to make decisions or to tell me what they wanted, Id just do what I really wanted on my own time. As an adult I became super narcissistic and my MO was to control people into doing what I wanted, and I never want to be that person again so…. I just sort of take a back seat with things. I explained that in my life I was always told people felt it was my way or the highway, so I was trying so hard not to be overbearing with her. She said she understands, but it comes across as very wishy washy  

she basically told me I am overanalyzing my own behavior and over-correcting, in her POV. She feels by doing this I’m invalidating myself and that with her, I don’t have to worry about any of this being “controlling” because she’s never do anything she didn’t want to do, and she wont. She told me she needs someone who can take control, for lack of better word, because her life has always been more rigid, some of it for bad reasons, but a lot of it just a byproduct of her career. She said she just operates best in that dynamic. 

this took me a moment to wrap my mind around  because I kept equating my needs as controlling, because that’s how I had previously expressed them for so long.  But eventually it sort of clicked in my mind, that she was telling me I can have my needs and verbalize them, and if she doesn’t want to go along with any of them, she won’t.  So it’s not to do with me being controlling, rather, relearning how to validate my own needs in a healthy way and allowing someone to interact with them 

there were some condiments on the table and I essentially laid some out and said to her that all of this is what I was doing, it was me wanting to give her options, I felt it was considerate. “Which condiments do you want? Versus me picking one for you and that’s what you get.  That seemed rude and inconsiderate.”  But then, I took the one I wanted and I put the other one she usually uses in front of her and said “you’re going to get this one, and I’m taking this one. Is this how you want me to talk to you?” And she said, “yes.” 
 

For whatever reason , finally, finally, this all has clicked in my head. It felt like all of the puzzle pieces fell into place and my confusion left me. I know many on this board have been drilling similar things into me but my brain would always go back to “but idk what she feels or wants and I need to be sure,” blah blah. but to hear this all directly from her, the very person I thought I was being “considerate to,” it just hit different.  She must have had me pegged for awhile now. And now I feel pretty free. Like, I don’t have to not have needs, or not express them for fear of being my former self. I can express what I want, and it doesn’t mean I’m controlling the situation or being greedy or narcissistic. They’re just my needs, my desires. And she’ll let me know if she’s not into going along with any of them, and that will be ok. 

[NighttimeNightmare]

18 hours ago, Kwothe28 said:

What would she enjoy more? Does she likes being around people or is more "homebody"?

If she likes to party and not spend New Year at home, go for a party. Even if you try something, you can do it there. 

She’s definitely not a homebody. I’m going to let her know I’m going to the other party and want her to come 

14 hours ago, rainbowsandroses said:

I'm sorry the NYE party was cancelled and agree with others that it would a nice gesture to invite her to your party or plan something entirely different.

I was wanting to but sort of on the fence as I didn’t know if she’d want to. But after our convo we had, posted about it above, I feel a lot more confident in letting her know what I want, which is her with me.  That’s what I want, so I’m gonna express that. She can come or not. But hopefully she does 

14 hours ago, rainbowsandroses said:

Good luck!  My new guy and I are off to the mountains for the weekend so hope y'all have a great time whatever you do.  

That sounds fun, same to you! Thank you 🙂 

[Kwothe28]

20 minutes ago, NighttimeNightmare said:

Essentially the gist of the conversation was that she said my attempts at being polite and courteous are coming across as a lack of interest. She said she never knows what it is that I want, because I don’t ever tell her.

And was it hard to say after that: "I want you". Godamnit man, stop sabotaging yourself...

[Wiseman2]

3 hours ago, NighttimeNightmare said:

I’m going to let her know I’m going to the other party and want her to come..

Definitely invite her sooner rather than later. Enjoy the party 🎉

[Batya33]

4 hours ago, Kwothe28 said:

And was it hard to say after that: "I want you". Godamnit man, stop sabotaging yourself...

I agree although perhaps a little more leniently.  I'd have realistic expectations -I get her gist but actually doing this in person with all the various interactions is going to be a lot of trial and error -not an exact science at all.  She wasn't sexist but she means -I think - be a man, step up to the plate.  But she doesn't want controlling - no one reasonably healthy does - controlling meaning to an extent where she constantly has to tell you to back down -I mean if she wants that level then maybe that's just what turns her on but I don't get that sense.  She simply is tired of the passive doormat approach that is dressed up -or intended by you -as considerate and nice.  

(And yet she didn't want to tell the man at the party/event to get lost -she wanted you to do that - didn't she say she knows how to speak up? Hmmmmmm)

Again -not an exact science at all.  I don't' think it has a darn bit to do with her career -I had a similar one for 15 plus years -she chose the career because it suited her personality -it's not a byproduct - it's why she chose it. I think that makes a difference.

I'm glad you feel positive about the conversation.