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I am clueless about how to proceed with this lady and I don't want this to be yet another catastrophe

Tagged as: Big Questions, Dating, Troubled relationships<< Previous question   Next question >>
Question - (2 October 2020) 10 Answers - (Newest, 7 October 2020)
A male Italy age 41-50, *uchosTacosyChurros writes:

Hello Cupids and Aunts. I am in need of advice for what I am more and more convinced is a mess I got myself into.

A while back while at a funeral I saw a woman who really really caught my eye, both for her beauty and her way of bearing herself. I managed to get an acquaintance of us to put me into contact with her but then I discovered she was already taken. It happens. However we remained in contact: sometimes I would drop by at her office for a short chat (announced) and we would text ourselves semi-regularly.

A while back, during the lockdown, we started texting ourselves more and more regularly (albeit she would often not reply but she has no obligation to me and we both have a business to run) and when the travel restrictions were finally lifted she invited me over to see her new office.

After showing me around the place, we went into her own office (she's the boss/owner), she locked the door and, completely out of the blue, she told me her common law husband had broken off their nine year relationship to go and live with a much younger woman (and a single mother to boot).

She understandably still sounded extremely angry and upset about the whole episode, so I tried to cheer her up, first by complimenting her looks and since I seemed to have embarrassed her, I asked her if, when (if?) travel restrictions will be lifted she would like to come with me on a trip in Japan. With that she really brightened up, said she has always fancied going to Japan and the conversation continued.

Sadly I also learned that her mother, who had already been gravely ill, had apparently suffered a relapse of her illness and her health conditions were again deteriorating.

After three weeks during which she rarely replied to my messages, I got one very early one morning saying her mother had just died.

I went to the funeral, which was a very private family affair: the only outsiders besides myself was a childhood friend (I think) with her husband.

I don't know why she asked me to come since she handled herself splendidly as the "man of the house" as her own father was understandably very upset, but I simply sat behind her the whole time, watched if she needed anything and finally when she went home with the rest of the family she told me "hear you soon" and it was the last time I heard from her.

Over the intervening two weeks I have sent her two messages, one asking if everything was fine and the other asking forgiveness if my little joke-telling session with her uncles sounded inappropriate. No reply, not even to tell me to bugger off.

I have been alternating between being very worried and very angry on the matter as common courtesy would dictate at least an answer but, again, she has never been reliable on that front and she probably has bigger fish to fry than me right now.

And here are a few extra data: we are both in our 40's, both financially independent, neither of us has children from previous relationships, and let's just say there's a bit of difference in our appearance. She's very beautiful, especially for her age (44), always well dressed, while I look like an ape which has been strategically shaven and put in an ill-fitting suit. My health is not good by any stretch of imagination due to a birth defect, but she knows this and she's apparently fine with it. I can live a more or less normal life, albeit with lots of dietary restrictions, regular check-ups and a few pills every day.

On top of this I'd like to add that my relationships with the other sex have been catastrophic to say the very least since I care to remember.

At this point I have no idea how to proceed but I have no idea what to do without causing yet another catastrophe.

Any advice is welcome, as long as it's quick: I fear I may lose this one just like I lost another.

View related questions: affair, text

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A male reader, MuchosTacosyChurros Italy +, writes (7 October 2020):

MuchosTacosyChurros is verified as being by the original poster of the question

I just wanted to thank all you people for your kind replies: I just come from three very hectic days at work, and things are about to get a whole lot more interesting... because I have been asked to help some Uni undergraduates with their graduation theses. Very exciting for me albeit I don't think anybody but a weirdo can get excited about teaching a bunch of very bright 20-something about the chemistry and physics of industrial composting!

Anyway I'll keep you updated once I have some news. Hopefully this will end in a bang (more likely a slap) and not in whimper. I like ending these things in style but this time... there's something about her I have never felt before. Of course only me had to get stuck in this kind of situation at 44.

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A reader, anonymous, writes (5 October 2020):

Corrected typos:

"She doesn't always need a man's shoulder to cry on; and may at times feel a bit of bitterness and disdain for our gender, and she's actually avoiding contact."

"I think her staggered-responses are just her way of letting you know she prefers limited-communication; and she will respond when she feels up to it."

*Maybe she doesn't want him to think she's seeing somebody!

Which she isn't!

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A reader, anonymous, writes (5 October 2020):

I concur with Code Warrior's assessment and opinion of your situation. She isn't leaving you hanging; she's controlling the narrative, and keeping things in proper perspective. She isn't stupid, she senses your attraction; and she realizes that frequent and regular contact can be misconstrued by some men. Some unscrupulous-types will seize on the opportunity when they sense vulnerability or weakness in a woman; and SHE IS in the midst of a very emotionally-charged situation, where her relationship was abruptly ended. It involves another woman, regardless of that woman's age. She has made it abundantly clear, she's not interested in dating you. Thus her contact is restrained. For whatever reasons, maybe she thinks her relationship is salvageable; and not interested in getting too emotionally-involved with other men. Respect that.

She could be preoccupied with attempting to salvage her relationship at the moment; and surely doing all she can to heal from whatever pain it is causing her. She doesn't always need a man's shoulder to cry on; and may at times feel a bit of bitterness and disdain our gender, and actually avoiding contact. Understandable under the present circumstances. She also has a business to run, and constantly whining about her relationship to you is pointless and self-defeating. Maybe self-pity just isn't her thing. You were at the right-place at the right-time when she needed to vent.

You mustn't presume that you have a closer connection than you do. By this I mean, you may feel closer than she actually feels towards you. If she quickly responded to your each and every contact; you'd get the impression that she's really into you. It's evident you're looking for signals and affirmations. I think her staggered responses are just her way of letting you she prefers limited-communication; and she will respond when she feels up to it. There are intervals in her busy-life that she will need a friend to turn to; and she knows you'll be there. Don't be discouraged, but don't get your hopes up along the lines of romantic-interest.

I think she is a strong woman. She is handling things in her own way, and isn't allowing herself to fall into emotional-dependency on you, or any other man. I think she refuses to be a burden on you, and she is capable of dealing with this matter with dignity and strength. She is mature and experienced; and may not be as devastated as she was at-first. Your support is helping. It's not as much about her aging as you might think. It's the principle of losing her long-term committed-relationship she has invested so much time and emotion into; only for it to come to this. You somewhat trivialize it to being about her vanity. You continue to keep it all relative to her appearance and age. Meanwhile, punishing yourself with self-deprecation about your looks; because you can't use this opportunity as a chance to woo her affections.

You'll hear from her when she needs the comfort and support of a friend. Just be ready when that time comes. Don't be disheartened that it may not be about any romantic-interest; or perceive being friend-zoned as a kind of rejection. Maybe this isn't as superficial as the fact you're not a dashing young hunk; but you're a man of character who she can count on to raise her spirits when she's feeling down. Don't lie to her, that's not how you earn trust. Deception is never justified, good sir! Making promises you can't keep, and creating expectations that will not materialize, is a sure way to lose her altogether! Don't treat her like a brooding child, or as if she's totally helpless.

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A female reader, anonymous, writes (5 October 2020):

Firstly you meet this lady at a funeral and decide to approach her. You find she's 'taken' and in a long term relationship. So, what do you do? You get her details and spend a lot of time trying to get between her and her 'common law husband.' You're not interested in being just s friend. You were hoping at this point to worm your way between them.

When he does actually leave her and she's upset, you don't step up and try to be a real friend, you USE the situation to try to win brownie points by asking her to go on a trip to Japan! Which you never intended to do anyway!

So, she's upset, understandably and you as a 'friend', LIE to her, (right at that moment when you should be comforting her, IF you were a friend) and ask her to go to Japan with you?! And WHY would you think this situation called for ANY kind of a joke?

Your judgement and your mind processes seem to me to be at the root of your problem.

Your latest follow up worried me. The phrase 'whether she likes it or not,' worried me a lot. She owes you nothing buddy.

This statement that you made, although I already suspected as much, confirmed to me that you do not care for this person, you care for you. You actually sound rather scary. I hope, for her sake, that you don't hear from her again.

I think that you try to make the right noises when trying to get into a relationship, but the fact that the other person actually doesn't REALLY figure in your emotions, comes across. With every post you made, you made that more obvious. All this, 'wanting to make sure she is ok,' is bunkum. You wanted to make sure she wasn't mad at you and that you still had a chance.

Oh and one last thing. You 'alternating between anger and worry,' over not getting a reply and caring about common courtesy made me laugh. I wonder how her 'common law husband,' felt about your lack of common courtesy, when you found out she was 'taken' at this funeral, but proceeded to text her on the side, hoping to get into her knickers!

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A male reader, MuchosTacosyChurros Italy +, writes (4 October 2020):

MuchosTacosyChurros is verified as being by the original poster of the question

Code Warrior: I have used the term "common law husband" because I am not from a Common Law country and I do this sort of stupid mistakes all the time. Legal terms and concepts are a bit different here.

The point is she has been together with this guy for nine years, they lived together for a while and then this stuff happened. There's no "marriage" as in "legally binding contract" and long term partnerships here have no legal meaning if there are no minor children.

Sorry for the lack of clarity.

I posted an answer before (which got lost in the shuffle apparently but I am a n00b and I have problems posting here) to the tune that my personal idea is she's ashamed and angry for having been beaten by a younger woman because it made her understand she's getting ahead with years. The whole Japan stuff was never realistic but, hey, at least she brightened up: the situation called for something different from the usual "a horse walks into a bar" kind of joke.

In my previous message I also stated that I don't mind if she just wants a shoulder to lean onto once in a while but... I will press her for a honest answer since she got into contact with me again yesterday and honestly I just need the "darker thoughts" to evaporate before having a very serious chat with her, whether she likes it or not. I am absolutely fine with the "just friends" stuff, not every story has a happy ending, but I am even finer with honesty.

Since we are at it, I think that at 44 this was basically my last huzzah. Oh well, at least she was very good looking and a great conversation as well.

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A male reader, MuchosTacosyChurros Italy +, writes (4 October 2020):

MuchosTacosyChurros is verified as being by the original poster of the question

Hi people and thanks for your answers.

I think I left out a few things.

My biggest bone right now is that I am very worried about her. Once I know she's fine, I can deal with everything else. If she wants to remain single, look for somebody else or whatever, so be it. I just want to know she's coping well with her situation: if she just wants a friend... well, friends don't leave friends hanging in the wind, right?

Yesterday I got a completely random message from her wishing me a good weeked. I am relieved since it means I haven't offended her at the funeral (or she got over it), and we'll talk at a later date, perhaps. Again, once I know she's fine and coping the best she can, so be it.

Then there's the whole office thing... well, I knew she wouldn't come with me from minute one (and I basically lied since Japan is extremely expensive and I am a notorious cheapskate) but she was so angry I just needed to take her mind off her failed relationship and I just couldn't make a stupid "A horse enters a bar..." kind of joke at that moment, right?

In fact I immediately suspected she had locked the door because she was ashamed of what had happened to her but she just needed to vent. I don't mean to be offensive but she got beaten by a younger woman: it means that, as beautiful as she is, time is passing for her as well. It mustn't be easy to stomach. Hence my stupid idea of complimenting her looks. And that wasn't a lie, I swear.

Don't worry, I am old and experienced enough to understand nobody, and I mean nobody, would fall for me just like that. ;-)

We'll see where we get from here but I suspect you folks are basically right: I am getting nowhere and fast. Oh well, guess some of us got a free lifetime subscription to that club at birth. Maybe I'll get better luck during my next life. :-D

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A reader, anonymous, writes (4 October 2020):

Sorry, I found a typo:

"It would only frustrate you, having the kind of self-image you have; yet you exclusively seek women according to their good-looks, when you claim your own appearance has its limitations."

Furthermore:

You may have some defects, as we all do. Don't allow them to make you believe women cannot see the kind and lovely soul beneath the surface; and still be attracted to you. Expect "catastrophe," if your main criteria is based on beauty; or if you fail to recognize when romantic-attraction isn't being reciprocated.

Don't offer women expensive gifts or bribes in exchange for their companionship; that places you in the position to be used or manipulated. She's apparently not that kind of lady!

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A reader, anonymous, writes (4 October 2020):

P.S.

If she does possess any romantic-attraction for you; you have to give her time to heal from her grief and loss. It tends to keep you on an emotional-rollercoaster; and your moods constantly fluctuate. She only wants to be in her best frame of mind when she connects with you, as her friend and comforter. I was not trying to take the wind out of your sails, or burst your bubble; I only meant to help you regain the proper perspective...just in-case. Her silence is time taken for mourning and healing. Don't take it personally as disrespect, or feel rejected.

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A reader, anonymous, writes (4 October 2020):

You're being appropriately kept in the friend-zone; and you're indirectly trying to push the connection further than she cares to take it.

She controls your communication and contact to let you know; this is not a romance, but a friendship. You have limited-access, and she might be trying to work things out with her ex.

Your feelings about your appearance is your cross to bear; and that should not be projected onto her. Unfairly presuming that her conceit limits her choices, or taste in men. She may not be that shallow; just because she may not be interested in a romance with you...or anybody else, for that matter! She is freshly out of a broken relationship; and she is healing from it...or trying to repair it. She could use a sympathetic-ear, but don't be an opportunist. She clearly has let you know, she is not the vulnerable-type.

If you wear ill-fitted suits, get them tailored to fit by a seamstress or tailor. If you have to shave strategically, what does that really have to do with anything? Dear sir, why would you compare your looks to an ape? What do you gain from self-degradation and putting yourself down like that? Stop it!

If all your attempted-relationships end in catastrophe; don't blame your looks, consider your personality and/or the type of women you tend to pursue.

In your post, you mentioned that she locked the door of her office during your visit. That was because she was about to discuss her personal-life with you. There seems to be some subtle implication that she was about to make a move on you. Her private-life is not public-information; so she closed the door. Nor was she suggesting or even hinting that she was free to date you. It is not what you may think.

Maybe you thought offering her a trip to Japan with you would be a romantic-enticement; that was sweet, but it only cheered her up. It didn't stir any romantic-feelings, as you must presume. It appears that her behavior is quite appropriate; and she is by no means leading you on. It seems to me you are quite captivated by her looks; and that isn't necessarily attributed to any true feelings for her. She obviously likes you, but keeps things strictly platonic.

I think you should understand that her time is preoccupied with running her business, dealing with her own grief, and her grieving-family; and perhaps that may include other family-matters. She got hit with a double-whammy, a breakup and the death of her mother! Plus her dad is acting-up!

I don't think there is a romance to proceed with, but I think you are becoming a good friend.

You shouldn't punish yourself for your appearance; or blame your birth-defects as the reason you cannot initiate a romance with this woman, or any other. If she doesn't feel that way for you, it isn't fair to blame your appearance as the reason. You may prefer to pursue exceptionally beautiful-women; because you have relatively good-taste, but your ego may place your standards higher than reasonable. It would only frustrate you, having the kind of self-image you have; yet you exclusively seek women according to their good-looks, when you claim your own appearance his its limitations.

You should let her take lead in this situation. She recently broke-up with her common-law husband. She has that to contend with. She was not initiating a romance with you, but leaning on a friend. So if anything, I would urge you to reset your mindset.

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A female reader, Youcannotbeserious United Kingdom +, writes (3 October 2020):

Youcannotbeserious agony auntI suspect the lady may indeed have "bigger fish to fry", i.e. mourning her mother and supporting her grief-stricken father.

In your shoes I would back off for the time being. Perhaps send her a message saying you hope she is ok, that you are not going to bother her as you understand she is mourning her mother. Then just add that, if she ever feels the need to chat, she knows where to find you. That takes the pressure off her and leaves the ball very firmly in her court. Then you need to leave it. If she doesn't make contact again, you know where you stand and you need to accept it.

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