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

[NighttimeNightmare]

My age-gap saga continues. Since my last major post about my much-older friend, a lot has transpired.  We’ve gotten really close and the constant phone calls have turned into spending that time face to face.  At first I would go to her house occasionally, but that has turned into more consistency, to the point it’s weird if I don’t see her. We cook dinner together at times, go shopping, run errands, visit interesting places, it’s just really easy to be around one another. 

im there for her if she needs me, and she has been there for me. Though it seems she wants more from me emotionally when she’s hurting, she seems annoyed when I’m overly logical or stoic in my responses. We actually got in our first real “fight”(if you could call it that) over this very recently.  But I don’t know what more she wants from me, she says a shoulder and for me to listen… but that makes me feel even closer to her so I try to avoid it because I know at some point she will meet someone and this all ends  

a lot of the time it feels like we are more than friends, this is something I’ve always felt to some degree, but now it’s more intense. I’ve met her friends, she’s met mine, another one of her friends invited me to dinner at her home a couple of weeks ago, and the discussion has come up between the two of us about how everyone thinks we are in a relationship.  I told her I was aware and that it doesn’t bother me. I don’t know what it feels like for her, one of the neighbors asked if I was her son, and once when we were out the cashier referred to me as her son. We’ve been out to dinner quite a bit at this point and I’m not really phased by peoples opinions.

She likes to do little things for me that I think are sweet gestures.  For instance, I forgot my unpotted plant at her house one evening and she surprised me with a new pot for it that she got for me, it was potted when I walked into her house and it just made me really happy that she had done that.  I mentioned one day I like chocolate only if it has a filling, and she picked me up some chocolate with caramel and sea salt.  Etc  I do things for her too, it feels mutual 

at the house there’s been some mild flirting on and off, like, I found her photo album with a few risqué shots, she’s thrown a book in front of me and said “this is fun,” and when I looked it was a soft porno about a mile high club.  And more recently I went over one night to drop her birthday gift off and the cleavage was more than I’d ever seen before.  I tried really hard not to focus on them. Some days it’s REALLY difficult to not make a move on her, but I keep those feelings to myself  

i don’t really understand what we are doing. Sometimes, after we’ve had a particularly fun day together and wind down for our nightly talk, she will say something like “… you know we’re 30 years apart” and pause as if she wants me to comment. Or some reassurance, I don’t know. Not often does she say this, but it’s notable. And a couple of weeks ago she told me her friend wants her over for Christmas dinner and also wanted her to meet her brother. She went on a rant to me about how she isn’t interested. We were just sitting down for dinner and felt a type of way and changed the topic. Because she can say she isn’t interested, but one day she’ll meet someone she is interested in, and that means I go away 

I always thought I would be happy for her, and I wouldn’t feel anything, when that happened. That maybe I’d even be relieved.  But well, tonight was Christmas and they had the dinner. And I didn’t hear from her. Usually even if we don’t talk or see eachother during the day she sends me a quick goodnight message. So maybe it went well for her, but I found myself feeling sad at the prospect of that being the case - of her finally meeting someone and of this ending.  
 

I don’t think I realized how attached I had gotten to her. In fact, last night she called me really late and I could hear she was driving. She told me she had just dropped her best friend off who was visiting from out of state. She asked if my ears were burning. I asked why and she essentially told me the two of them were talking about me and she was telling her how amazing and talented she thinks I am. I sometimes think she’s attached to me, too 

but right now I’m pretty sad and don’t know what to do with my emotions. Even if the brother was a no-go, there’s always someone else.  It’s only a matter of time 
 

 

[Kwothe28]

36 minutes ago, NighttimeNightmare said:

but right now I’m pretty sad and don’t know what to do with my emotions. Even if the brother was a no-go, there’s always someone else.  It’s only a matter of time 

Well yes, because you wont make a move.

Is she suppose to wait for you until you are ready? Its clear that you have emotions there but you are afraid of acting on them. So that leaves her in eithe waiting for you(no sane person will do that when you just dont show that you like them btw) or moving on. So in time she would move on.

That leaves you with either trying something and see what it could happen for better or worst. Or be in friendzone when she finds somebody else. I suggest you at least try. Its much beter then to ever wonder "what if". Even if she says "No". And its better then to be around while she finds somebody else. Its not a solution for your prroblems.

[Lambert]

If you aren't interested in a romantic relationship, then end it. Sometimes we have to be cruel to be kind.

[Batya33]

I'm sorry you're feeling sad and I hope you feel better.

[Wiseman2]

It seems like you two have grown very close and you would miss her if she started dating someone. However she's not necessarily dating anyone at the moment. 

[NighttimeNightmare]

5 hours ago, Lambert said:

If you aren't interested in a romantic relationship, then end it. Sometimes we have to be cruel to be kind.

I do want that with her but I’m pretty sure she doesn’t want one 

 

which now that I’ve typed that out is kind of weird that I’m so certain she’s now potentially in the beginning of one with another man.  Maybe it’s just me she doesn’t want one with 

[Lambert]

27 minutes ago, NighttimeNightmare said:

I do want that with her but I’m pretty sure she doesn’t want one 

 

which now that I’ve typed that out is kind of weird that I’m so certain she’s now potentially in the beginning of one with another man.  Maybe it’s just me she doesn’t want one with 

ok. I misunderstood the problem.

In this case I would tell her how I feel and that if she isn't interested then, sorry you have to move on. 

It's super hurtful to you to remain in this situation. You can't sacrifice yourself for her.  In the long run you'll kick yourself for wasting your time with a dead end situation. 

Believe me- I know it sucks.  I was seeing someone and thought it was going great.  He ended up saying that I checked all the boxes for him, BUT not in religion. So he ended it.  Which i am kinda mad about it because he knew my religion was not the same as his. So why even start anything... but what can be done? nothing. let them go.  This too shall pass.

[ShySoul]

Sorry if this has been said on a prior post, but has she specifically told you she doesn't want more? Because deep clevage, flirting and handing you porn doesn't seem like things someone does with someone they have no interest in.

If going on as things are is causing you this much pain, then you need to change the situation. Tell her what you feel. Lay it all out. The biggest regrets I've ever had is when I said nothing and was left to wonder what if. When I've gotten my feelings out I've always felt better, even if things didn't go the way I'd hope. Maybe she will want the same. Maybe just the act of talking about it instead of dancing around the subject will help you feel better. Maybe if she doesn't want more, you can work out a way to cut back and avoid doing things that feel to intimate. Maybe you will need time apart to heal. But you won't know any of that unless you actually talk everything through. What you do know is that the way things are is hurting you. And something tells me she wouldn't want you hurting like that.

[NighttimeNightmare]

I can’t stop the intrusive thoughts and I’m spiraling.  I bet she’s on a lunch date with him. 

[Wiseman2]

8 minutes ago, NighttimeNightmare said:

I can’t stop the intrusive thoughts and I’m spiraling.  I bet she’s on a lunch date with him. 

Has your usual level of communication dropped off? 

[boltnrun]

Self-flagellation does nothing to help your situation.

Do you feel you don't deserve to be happy, no, that you deserve to be UNhappy?

What would you prefer, to keep your mouth shut in an attempt to keep her in your life as a "friend" and potentially witness her dating other men or shoot your shot and take the chance she'll feel the same OR will kindly explain she doesn't feel the same?  Limbo or knowledge, your choice.

And BTW, you have zero evidence she liked that man.  Torturing yourself with imaginary dates she's going on does no one any good.

[NighttimeNightmare]

22 minutes ago, ShySoul said:

Sorry if this has been said on a prior post, but has she specifically told you she doesn't want more? 

Not necessarily because I’ve never told her I had feelings in order for her to say “no thanks.”  It’s moreso in her generalized comments.  For example, when we are watching shows together and a dysfunctional couple scene comes on, she will say “see this is why I don’t want a relationship.” It’s things like that. But then other times she will say she could have one, maybe.  She said that to me the first time i hung out with her at her home. I was sitting on the couch, we had gotten home from having dinner together, and she walked over to me and said “my friends say I couldn’t have a relationship, but i think I could.”  On the flip side to that, she again has told me “so I’m supposed to just open my heart up and get hurt?”  She just sort of jumps back and forth between the two. I get it, because she had a really really bad experience. And I mean, I’m not particularly interested in hunting for a relationship either, I’ve been ***ed over too, but when I’m with her I do have the thoughts that with her it might be nice.  Esp since we’ve already naturally sort of have fallen into a routine.  She says she was trying to avoid feelings (again in a general sense) and so was I, hell I still try to, but there are already feelings.  She got so hurt the other day over something I did, or rather didn’t do. So trying to avoid ‘feelings’ isn’t working either. It’s like she wants more from me but then she doesn’t realize what constantly saying “I don’t care for a relationship” has done to my thought process so why would I try to give her more, then she got mad and hurt that I was dismissive 

31 minutes ago, ShySoul said:

Because deep clevage, flirting and handing you porn doesn't seem like things someone does with someone they have no interest in.

I don’t even know, maybe it’s just fun for her but we don’t touch the elephant in the room. Moreso beyond the playful flirty things, it’s the emotional intimacy that makes me wonder about everything.  We regroup with eachother, I’ve gotten to the point where I am vulnerable with her about things going on in my life and she shows up for me. My alarm system failed in my car the other day and I couldn’t get the car to start and I called her and she dropped what she was doing to come get me. I’m supposed to be going to her house tomorrow to be there when the repair guy comes in, so we definitely rely on one another. 
 

the flirty stuff is just some subtle bonus. To be honest, I was shocked when she opened the door in her robe. She was nude underneath, I mean I knocked on the door at 9pm and didn’t tell her I was coming over so it makes sense she was in her bedtime attire. But she took forever to answer the door and I figured she would have changed.  The energy doesn’t feel sexual to me tho, so it throws me off. 

36 minutes ago, ShySoul said:

If going on as things are is causing you this much pain, then you need to change the situation

I know this is true and I’m tired of being stuck in a loop. I mean, when I first met her I was stuck in a loop and managed out of it and let life unfold how it would. And we just got closer and closer. I’m happy when I’m around her, and I’m happier with her in my life. But then when things like this happen, I do spiral probably because I’ve avoided discussing this and it is “unknown” and I don’t do well with a loss of control but now I’m realizing the real effects of sweeping this stuff under the rug

[NighttimeNightmare]

9 minutes ago, Wiseman2 said:

Has your usual level of communication dropped off? 

I’d previously had said yes but I think this is my anxiety blowing a situation out of proportion, because it’s only been a day, it’s not like I haven’t heard from her in weeks. I’m recognizing this logically, however, I can’t stop my mind spiraling 

I mean, sometimes I don’t hear from her for a bit and then she will call me and tell me what she’s been up to. So logically, that is prob what’s going to occur, she will probably call me in a few hours. But what if she doesn’t? Because she met someone. We usually don’t go more than 2 days without a phone call and usually we text daily. That’s our normal but sometimes there’s variations to it.  
 

She txtd me yesterday morning, I knew she was on her way to the Xmas dinner so I didn’t txt beyond wishing her merry Xmas. Then around 11pm I hadn’t heard from her so I txtd to ask if she was still partying.. no response.  Now it’s past the time I usually hear from her the next day. Again, she has done this before, so it’s maybe normal, but my mind is saying she’s prob on a date with this dude. Why isn’t she texting me 

it’s very rare that I get like this. I just don’t know how to stop it. I won’t txt or call her cos it’s not her responsibility to soothe my disregulation.  I have to figure out how to stop this, this isn’t her fault or anything she’s done.  She has 0 idea I’m struggling 

 

 

[ShySoul]

So it's a little bit of a different situation, but I can relate to what you are feeling. I became friends with a woman and we would chat online and on the phone for hours every night. Distance and schedules kept us from seeing each other in person often, but we tried to see each other when we could. Mutual feelings developed. Eventually we had to say something to each other, because we couldn't hold it back any more. Even then, she would keep pulling away in part because of her past experiences. Then we would get close again and it would be like we were on the completely same wavelength. The mixed signals would drive me mad. 

What helped me though it all was being honest with my feelings and letting her know. If I had not said everything I was feeling, good and bad, it would have eaten me up inside. I would have tortured myself wondering what I could be doing differently, what went wrong. She didn't realize just what her actions were doing to me. Me calling her on it actually got her to (eventually) look at herself and admit things she was avoiding. Ultimately it didn't work out, but I can look back on it and realize that I was better for going through it and that opening up about my feelings  was the best thing for me.

As you said, feelings are already there, seemingly on both sides. The only way to deal with it, is to actually talk and deal with it. Even if it brings some hurt in the short term, it will be better in the long term. 

[Tinydance]

I'm sorry if this sounds blunt....You always said in all your posts that you feel disappointed that nothing romantic is happening with this woman. You've written a lot about it and you're very frustrated. I'm sorry but you can't keep complaining that nothing is happening because you haven't actually made any move or told this woman how you feel.

I think she's into you in *some* way that's not only platonic or sibling like. If she thought of you as her little brother or good buddy, she wouldn't send mini skirt photos, show cleavage, show porn book, flirt, etc. She thinks of you as a man, as some kind of sexual interest or admirer. I 100% guarantee you that part. She's sending you some kind of sexual signals and you always do absolute diddly squat about. Now she's going on dates with another man because she's getting nothing from you. Stop complaining and start doing.

[Wiseman2]

6 hours ago, NighttimeNightmare said:

. I just don’t know how to stop it. I won’t txt or call her cos it’s not her responsibility to soothe my disregulation.  I have to figure out how to stop this, this isn’t her fault or anything she’s done.  She has 0 idea I’m struggling.

It's great you have insight into the situation that it has nothing to do with her. And that your dependence on her friendship and attention has become a bit of a problem. 

I don't think "making a move" on her is a good idea, since she's shut down some of your racier sexting, and was offended by it.  She doesn't seem interested in a romantic relationship whatsoever and at some level you know that. 

You also seem to know if you act on your obsession or sexualized feelings you'll destroy the friendship. She's not out dating other men. This is your imagination and obsession running amok. But you have insight into this. 

[shouldhavelearned]

What is it that you want from this relationship?

[NighttimeNightmare]

13 minutes ago, Wiseman2 said:

I don't think "making a move" on her is a good idea, since she's shut down some of your racier sexting, and was offended by it

She said a heart emoji made her feel awkward. But that was months ago when we first started talking and she was drugged up so I don’t even know how realistic any of that was.  But around that same time she let me call her sexy and say I was gonna j*ck off to her pics and wasn’t offended by that. Again… this was when she was on different meds so I’ve let that go as something in the past that is neither here nor there 

 

since then.. she’s gotten her medical stuff taken care of and is back to normal. A lot has changed since I made that post. Just the other night at her home when I found the photo album and I tried to look at some of the hidden photos she was laughing and told me to stop and give her the album.  I said come on let me see one. Then when she showed me, once again, I was like “damn that’s sexy” she didn’t stop me, she certainly wasn’t offended. In fact, that same night was when she first threw the soft porno book at me.  She’s engaging this.  She has thrown that book at me twice so far. What’s changed s now this mild flirting is also intertwined with an emotional closeness we’ve developed 

18 minutes ago, Wiseman2 said:

You also seem to know if you act on your obsession or sexualized feelings you'll destroy the friendship.

Yes, I do think if I make an actual move she will reject it. I don’t think it will destroy the friendship on her end necessarily, but it will on my end cause I’d stop spending so much time with her. 
 

 

34 minutes ago, Wiseman2 said:

She doesn't seem interested in a romantic relationship whatsoever and at some level you know that. 

She wants something. I don’t know if it’s romantic or just a deep emotional connection. We’ve had some rly deep emotional discussions, sometimes it’s prompted by one of us igniting some feelings from our past. For instance, she’s told me I did something that sort of triggered her back to when she was with her ex husband and it scared her. And she told me how much she values our connection and never wants there to be any walls between us. I told her I’d never do to her what he did to her. 
 

Romantic, I don’t know. Relationshipy-feeling.. yes. But I do not think she would actually make a commitment; that part is true 

[NighttimeNightmare]

4 minutes ago, shouldhavelearned said:

What is it that you want from this relationship?

To go further, we are getting emotional needs met from one another without any sort of commitment or discussion about what we are doing. I’d prefer to have some sort of committed relationship with her. I don’t think she would do it so… I’m just here venting about my feelings 

[Tinydance]

9 minutes ago, NighttimeNightmare said:

To go further, we are getting emotional needs met from one another without any sort of commitment or discussion about what we are doing. I’d prefer to have some sort of committed relationship with her. I don’t think she would do it so… I’m just here venting about my feelings 

Well you won't get any progress because you don't actually want to do anything about it. And if she's going on dates with other men she might be with someone else. Your window of opportunity might be closing so I think you either need to go for it or accept it as friendship only.

[NighttimeNightmare]

1 minute ago, Tinydance said:

And if she's going on dates with other men she might be with someone else

She told me she isn’t going on dates with people.   This post is just my feelings prompted by the fact she told me that her friend is trying to set her up with her brother and that he was going to be at the Christmas dinner she was invited to. She told me she was annoyed and not interested.  But that could all change if he striked her interest at the dinner.  Which is what I think happened. It’s my anxiety but it could also be real  

and she’s definitely not with someone else. We spend all of our time together. There is no one else in the picture… yet. 
 

6 minutes ago, Tinydance said:

Your window of opportunity might be closing so I think you either need to go for it or accept it as friendship only.

True 

[Tinydance]

9 minutes ago, NighttimeNightmare said:

She told me she isn’t going on dates with people.   This post is just my feelings prompted by the fact she told me that her friend is trying to set her up with her brother and that he was going to be at the Christmas dinner she was invited to. She told me she was annoyed and not interested.  But that could all change if he striked her interest at the dinner.  Which is what I think happened. It’s my anxiety but it could also be real  

and she’s definitely not with someone else. We spend all of our time together. There is no one else in the picture… yet. 
 

True 

So are you planning on never doing anything until she's no longer single?

[rainbowsandroses]

1 hour ago, NighttimeNightmare said:

To go further, we are getting emotional needs met from one another without any sort of commitment or discussion about what we are doing. I’d prefer to have some sort of committed relationship with her. I don’t think she would do it so… I’m just here venting about my feelings 

Bolded - a bit hard to believe since you haven't acted in a way that would reflect you would prefer a committed relationship with her.  In fact, you have acted the opposite of a man desirous of a committed relationship with her.

A man who desires a committed RL with a woman would either be making that clear through his actions and/or words (preferably actions) OR if she is as commitment-averse as this woman appears to be, he'd be wishing her well and moving on.

So I am sorry @NighttimeNightmareI don't actually believe you want a committed relationship, I think you are fine with the status quo and so is SHE.  

I think you are both afraid.  Afraid to open up and be vulnerable.  That is what this boils down to imo -- FEAR.

She talks about not wanting to get hurt, you have expressed to us your fear of getting hurt, well yes that's the risk we all take when we choose to embark on a relationship and you are essentially two peas in a pod in that regard; you are on the exact same wavelength which probably explains your attachment to each other AND imo your mutual attraction.

But you're both too afraid to step up and do anything about it so you tip toe around it, hint about it, toss out suggestive comments here and there from time to time.

It's all very SAFE, emotionally, which beats the alternative I suppose - actually making a move towards what you SAY you want, which is a committed relationship.

I know my posts can get sort of "deep" sometimes but I've witnessed this type of dynamic between individuals who are attracted to each other and who feel a connection which clearly you both do, but too scared to act on it for whatever reasons. 

I have actually been there myself so I understand.  I've read books on it, one of which I recommend you read, you BOTH read, entitled "He's Scared, She's Scared, the Hidden Fears that Sabotage Our Relationships."  Note the word 'hidden' which is what such fears often are.  You both exhibit classic signs which the book explains in great detail.  I have learned a ton from reading it and I still read it from time to time to this day.

I am in a new RL now and reading it!

I dunno NN, it's up to you.  You have a choice.  You can either take a risk OR you can continue going along playing this game with each other whereby you both pretend you're just "friends" and hiding your true selves from each other.

I wish you luck whatever path you choose.

[ShySoul]

"Of all sad words of tongue or pen, the saddest are these, "It might have been." John Greenleaf Whittier

It's natural to be scared to open up. It's fine to vent. But if you keep doing the same thing, you'll get the same result. At some point if you want more with her, or even a chance at it, you have to speak up. Otherwise you will lose the chance, possibly forever. And the hurt of always wondering what might have been is worse then anything else, believe me.

[Wiseman2]

2 hours ago, NighttimeNightmare said:

 she let me call her sexy and say I was gonna j*ck off to her pics and wasn’t offended by that. Just the other night at her home when I found the photo album and I tried to look at some of the hidden photos she was laughing and told me to stop and give her the album.  I said come on let me see one. 

This has nothing to do with commitment and nothing to do with tiptoeing around or being afraid. If anything it's too bold and crass. There's nothing to "go for" here. She tolerates your over-sexualization of her in exchange for company. Please step back on the sexual innuendos. 

You seem to have this "naughty little boy" attitude toward her with she "let me" do this, she wasn't wearing undies, etc. Almost like a schoolboy. Maybe it's amusing or flattering to her, but definitely hard to take seriously.

However there's not much here to indicate she wants a romantic relationship. A one-sided over-sexualized friendship, maybe.... because that's all your offering.  And yes, when she meets a mature man who treats her like a lady and seriously, you may see less of her. 

It doesn't even seem like a "age-gap" problem because even if you were the same age it would be hard to understand why any woman would tolerate this.  Sorry if this sounds like a wake-up call, but trying to help you snap out of this.