Weird behavior from MM

[WillaLewis448]

So, I’ve posted here before but I’ll recap everything here.

 

I’m 20, work at a coffee shop in NYC, and am a transgender woman (I haven’t gotten surgery yet though I really want to, this is pertinent). I had this customer for a year, he lives a block away, he’s 51 and married for a decade. As he’s told me, he found me good looking from first meeting me and he used to try to talk to me but I didn’t really pay him any mind until the spring when I began taking hormones and feeling better about myself and more confident, I guess. Around the summertime, our talking became open flirting. I note that around this time, he stopped bringing his wife into the store.

 

In October, I gave him my number and he texted me and we started basically an emotional affair with plans to kiss when we saw each other (he has health issues that recently have prevented him from leaving his house very much, walking is excruciatingly tough for him and he’s occasionally alluded to not having very long time left but he won’t specifically name the health issue). The first week we talked I realized he didn’t know I was trans so I told him. He was very respectful and has continued to be so, although he brings it up sometimes. We continued to talk, he shared a lot about his abusive childhood and life and stories and songs he’s written / made, he openly said that he’d shared more with me than anyone else combined, including his wife. I asked if he’d still be okay with kissing, he said that while transgender women weren’t his thing, he saw me as a girl and felt close to me and would be happy to. Halloween night we did meet and make out.

 

In November we continued talking and he got me involved in cryptocurrency investments. He had been telling me about them in October, even saying that he’d find something for me to do, and that him gaining financial stability would allow him to throw money my way.

 

Thanksgiving, I drunkenly sent him a text, “eventually I can’t wait to suck you” which his wife almost saw, but she did not. He got pissed and said we weren’t pursuing anything romantically but we’d stay close and continue our friendship and crypto endeavors. We argued about that and after a day, when sober, I told him about how I felt that we had a real chemistry and connection and that compromising future kissing felt unfair. He said he got how I felt but that continuing to kiss would be ‘entering into ****ty behavior’ if his wife was going to know we were doing crypto together. I told him I would be onboard but that it’d be hard with my feelings for him but he was kind of dismissive at that, saying it wouldn’t be that hard.

 

We continued doing crypto, texting everyday, and he was affectionate in the same way he had been before the debacle of Thanksgiving, calling me my dear, babe, saying to be continued, asking me if I missed him if I didn’t talk to him for a day. 12/10, while I was drunk at club (but very aware and coherent), I told him that he was “among the people I loved” and that he had touched my heart and I couldn’t bear for him to ever dump me like trash or stop being my friend. He told me that even beyond crypto, I “could not get fired”. He would also tell me he cared about me a lot and wanted to help me earn money so that I could get my surgery.

 

My ineptitude with crypto caused a lot of mistakes and it turned out to be a ‘nightmare’ in his words. He told me a number of times that he only continued to do crypto with me because he liked me and that with anyone else, he would’ve ended the deal. Nevertheless, he’s been very generous giving me money indirectly through coins (I’ve asked him if he’s that generous with his other friends - he is not, he sells to them for discounted rates but he always says that he wants me to benefit from him doing well and that he doesn’t want me to spend money).

 

For Christmas, I bought him expensive cologne he wears from Hermès. I had asked him about a potential gift he’d like the second day we texted. On 12/30, I met up with him after hours at my job en route to a club. It felt weird seeing him after about 7 weeks and still kind of on shaky ground. He kissed me on the cheek and I guess I leaned into him a bit. At one point walking, we were hugging and he asked me if I was nervous. I asked him if he remembered what I had told him (referring to my loving him) and laid my head at his neck. I walked him home and a few steps away from his building, we hugged really tightly, him caressing my back. My coworker walked by and drolled out “Good night”, and then as he pulled away, I kissed him. He kissed back and then went up to his building.

 

We continued to text in the New Year, though not as frequently. Usually, he would initiate conversations and tell me how busy he was with crypto and tell me he was thinking about me in the interim. I saw him with some guy on the street one afternoon and in my haste to get to work and not to make waves, I waved and quickly ran away. The next day he came to my job. I went on my break and we walked around the block and chatted; he wanted to know why I had avoided him before, he didn’t buy that I was rushing to work. Then as we said goodbye, I hugged him and he slightly turned his head so I wouldn’t kiss him on the mouth. He didn’t seem upset or annoyed.

 

The next day, I sent him a long message clearly telling him that I was in love with him and that was the cause for my nervousness and unease around him. I told him I wasn’t looking for him to love me back, just to care about me. I also told him I didn’t need a response immediately, though that part I was kind of hoping he’d respond sooner rather than later.

 

We continued talking about crypto until one day, I picked a bit of a fight with him, asking him how his wife was and calling her, his dear (he always calls me my dear), and calling myself an employee and saying he was my boss. He got really pissed at the employee and boss talk, saying I was not an employee and not to call him boss. Finally it turned into this thing where he revealed that he was kissed off at what happened on New Year’s since he felt that it was obvious to my coworkers that we had a private connection and that wasn’t discreet. He said he was mad but not at me, and that it wasn’t worth discussing hence why he didn’t mention it. He also said that kissing me would be wrong and that he had been clear that making out on street corners wasn’t in his playbook and that he’d been clear about his apprehensions from the jump (when he had hugged or kissed me on a street corner at Halloween, he initiated it - I was weary of hugging or kissing in public). We got angry at one another, me hurling that I was fighting so hard because I’m in love with him and him saying there was no reason for my hostility since he had bent over backwards for me more than anyone else and cared a great deal about me. He got annoyed when I said he was lucky to not be going through any pain in this situation and to have two women who love him unconditionally and said I was making it into a contest.

 

Things cooled over the next day and I sent an apology that was kind of overkill and way too eager for his attention and willing to take the blame for everything. He then sent an email that was nicely written but had issues, kind of throwing my being trans in my face and the fact that he kissed me in spite of his own less than progressive views. He also asked me to delete our correspondence and said all we really had was a friendship where we kissed once, and that he wanted to help me just because when he was younger and being abused, no one really helped him. He also accused me of not respecting our friendship and said that my asking him about kissing made him uncomfortable. At first I took this email at face value but then saw how he threw in his childhood abuse story to elicit sympathy and questioned whether anyone would really give tens of thousands of dollars to a friend. I also called crap on his discomfort about me asking him about kissing, I went back and read the texts and saw that I asked him gently two times, once the night we kissed and another time when he came by my job when I wasn’t there. Neither time did he say no and he always tells me how I make mistakes or says he can tell me like it is so he very well could’ve said no each of those times.

 

We’ve continued to text and do the crypto as well, despite my ‘help’ being a nightmare to him. Lately, I’ve ignored or not responded as promptly to his texts like I used to, at which he’ll hound me kind of incessantly to get in touch with me and call me on the phone and speak for hours. He told me how his wife now knows who I am, at least that we’re working on crypto together and thusly texting a lot. I asked him if he told her about Halloween, he said he did not.

 

Now I’m in a place of confusion. I don’t understand why continuing kissing the few times (to illustrate, I’ve seen him in person 6 times since I gave him my number October 10) I get to see him in person is ‘****ty behavior’ or ‘ongoing deceit’ yet he is lying about how we got to be close enough for me to work on crypto and I can guess he’s not telling her how he gives me money through crypto, especially with the intent to get me to Thailand for surgery by this May. And now that I know she knows my name and who I am, I feel guilty for being in love with her husband. I’m upset that he wouldn’t consider my potential guilt or apprehension in telling her. I also don’t understand why he’d do so, now if she ever found out about the full extent of our relationship, she’d be mad he cheated at all and then also hurt that he tried to lie and act like the two of us have nothing going on.

 

I’m also frustrated because he says he wants to be just friends but all of this doesn’t feel friendly or normal. First off, what kind of friendship does a 51 year old married man have with a 20 year old single woman? Especially one that he is emotionally intimate with (in a way he freely admits he hasn’t been with anyone else including his wife) and has kissed multiple times? Also, him trying to help me make money, essentially paying for my surgery with earnings from crypto, none of that seems like purely platonic friendship. He continues to text me and gets annoyed when I don’t respond promptly or ignore him for a day and hounds me, that doesn’t like pure friendship either. If we’re just friends who kissed once, why am I expected to respond at his beck and call. He also offers to send me Ubers for when I am coming home from clubs - he says I can text him, yet another reason for me to chat with him. I don’t think he’s doing that for his other friends. Plus why would he give me money freely, especially when I don’t ask. He’s also offered to give me money when I told him my hours were cut and money was tight, in light of everything, that doesn’t seem platonic. Regarding money, I never asked him to get me involved in crypto and I can’t figure out why he’ll even mention how he wants me to benefit from his doing well or why he’d continue to create reasons for me to talk to him and do crypto jobs for him, talking to him and earning money. I appreciate it but all of that doesn’t seem like friendship. Plus there are days where he’ll hammer how my doing crypto with him has caused him a ton of stress and that if it were anyone else, it’d be over. Why then does he get really mad and upset if I refer to myself as his employee or him as my boss? He says doing anything in his backyard would be the last thing he wants to do, yet he fully engaged in all of this with me knowing I worked close by and did initiate a kiss with me in said backyard. He says transgender women with male genitals aren’t his thing - yet he could’ve ended things with me entirely or not kissed me. If we’re one big happy crypto family, me, him, and his wife, why is he continuing to be kind of dishonest about me and why isn’t he bringing his wife around me or why is he telling me to delete our correspondence if we’re just friends and he’s never been misleading at all?

 

This is a lot but I really need help figuring this out. I love him and tell him I love him every time I speak to him. He says that doesn’t make him feel uncomfortable or awkward or weird. All of this is just a lot of mixed signals it feels like- I don’t know why if he’s done with the affair, he continues it of his own volition? If it’s over, let it be over. But don’t create reasons for us to be in each other’s lives. And I don’t buy that all his helping me is purely selfless to simply be like some kind of genie or Saint and send me off to get the proper genitals and make money for the hell of it. I don’t know why he keeps me on the hook. Thoughts?

[seren]

Hi Willa, it sounds like a jumble TBH, on the one hand you are involved because of your co interest in crypto currency and the other over blurred boundaries which see him attracted to you as a woman. Then he is told you are pre op transgendered, I imagine that came as a surprise to him and gave him cause to question his feelings.

 

I am just surmising here and no slight is intended to you or any other trans women or men, I have a few friends one male and one female trans who have experienced similar situations. Not everyone is comfortable dating someone who is trans, some feel guilty for their feelings, some love so much that they see the person rather than the gender and some don't.

 

I suspect that this and his guilt at having feelings for you while he is married is also a factor, yet you and he have a shared interest and what reads like a friendship. His age might have a lot to do with his outlook, many young people are more accepting of difference. It reads like initially, before you told him you were trans he was starting on the road to being more than friends, this seems to have halted once he knew.

 

You don't say if this is your first time to feel love as a woman, and maybe you read into it more than he could return, I can understand that. It is a huge leap for someone of 51 to get into the head space of dating someone who is Trans, he has lived thinking he is a heterosexual male and here he is having feelings for a Trans woman, who he might never accept not even post op. Not intending to be cruel, it's just a conversation I have had with a male friend who was in a similar situation with a Trans woman.

 

TBH, I would get away from him, you don't need to feel rejection and it doesn't sound like he is ready for your relationship to change and he is still married, I can never condone affairs. I hope your op goes well for you and you have a wonderful life with someone who loves you and feels comfortable kissing in the street for all to see. take care seen x

[WillaLewis448]

Thank you for the reply.

 

I still don’t understand why he would give me so much money for my surgery and beyond if he just felt like a friend. Same about the constant texts or getting mad about me wanting to keep things on a crypto only basis and calling him my boss.

 

I can understand him being put off by me being transgender, that’s fine and would solve much of the angst and drama. But he keeps stoking the fire, looking for reasons for me to be involved, he keeps mentioning sending me to Thailand. If it’s a dealbreaker then just let me go entirely, don’t have one foot in and spend over $15000 on me for no reason. How would his wife feel about that? I can’t figure out what he’s trying to do?

[skywriter]

WillaLewis448

 

The first big issue I read is the 31 year age, add to that he is married and then you being transgender. I don't say this to be cruel, however, he realized, that he shared a genuine friendship with you and chose not to allow these obstacles to interfere.

 

Obviously, he wanted to help you, as he got to know the person you are and he cares about your future. He is also mature enough to realize that he is married and he doesn't want to compromise his relationship with either you are his wife so he's steering things back on course.

 

I hope you can value this man as a friend and keep it as a friendship. He seems like he wants you to be successful in your future.

[anika99]

The MM is conflicted. Obviously he has romantic feelings for you that go beyond normal friendship but he is struggling with the idea of cheating on his wife and with being attracted to a transgendered woman. He is attracted to you but his conscience is holding him back.

 

At 51yrs old he should be the mature one and put a stop to this but doesn't look like he is going to. That means it's up to you. Your relationship with him isn't going anywhere. He's not going to leave his marriage for you and you would be wise to walk away from him altogether, however you probably won't do that either given that he helps you financially. Is the money worth the pain?

[CantTakeMySmile]

I don't know the link, but this man poster her within the last week. You should read to gain clarity,

[CatMinx]

He sounds more like a fairly creepy father figure than a boyfriend. Willa, are you sure you're not just latching onto this man because he's the first person who's accepted you and shown attraction towards you as a woman rather than because you actually have feelings for him?

 

I feel like it would be good to cut off this odd friendship and give yourself some time away from romantic relationships to adjust..and perhaps not with someone who is more than twice your age next time.

[WillaLewis448]

Hi Willa, it sounds like a jumble TBH, on the one hand you are involved because of your co interest in crypto currency and the other over blurred boundaries which see him attracted to you as a woman. Then he is told you are pre op transgendered, I imagine that came as a surprise to him and gave him cause to question his feelings.

 

I am just surmising here and no slight is intended to you or any other trans women or men, I have a few friends one male and one female trans who have experienced similar situations. Not everyone is comfortable dating someone who is trans, some feel guilty for their feelings, some love so much that they see the person rather than the gender and some don't.

 

I suspect that this and his guilt at having feelings for you while he is married is also a factor, yet you and he have a shared interest and what reads like a friendship. His age might have a lot to do with his outlook, many young people are more accepting of difference. It reads like initially, before you told him you were trans he was starting on the road to being more than friends, this seems to have halted once he knew.

 

You don't say if this is your first time to feel love as a woman, and maybe you read into it more than he could return, I can understand that. It is a huge leap for someone of 51 to get into the head space of dating someone who is Trans, he has lived thinking he is a heterosexual male and here he is having feelings for a Trans woman, who he might never accept not even post op. Not intending to be cruel, it's just a conversation I have had with a male friend who was in a similar situation with a Trans woman.

 

TBH, I would get away from him, you don't need to feel rejection and it doesn't sound like he is ready for your relationship to change and he is still married, I can never condone affairs. I hope your op goes well for you and you have a wonderful life with someone who loves you and feels comfortable kissing in the street for all to see. take care seen x

The timeline you have is off. He began flirting with me for a couple of months and a week into our texting, I told him I was trans. He kissed me after I had told him and asked him repeatedly if he was okay with kissing me in light of me being trans. Then he suggested getting me into crypto currency in order to make money, I did not ask him to get involved nor did I ever ask him for money. He’s the one that wants to help me get my surgery, I went along with his lead.

 

Does that make sense?

 

He continues to text me and now calls me and we converse for a long time, usually an hour or two. And despite my “being a nightmare for him”, he had me do some crypto work for him. Also, a few days ago he offered to come to my aid when I was coming home from a nearby (to his house and my job) nightclub on a cold night. He paid for a cab and insisted I not pay him back (as I would a normal friend). Just the other day we were discussing expensive watches he likes (upwards of $10000) and he said if our investments do well, he’d buy me a watch.

 

Why does he keep being inappropriate (regarding the boundaries of pure platonic friendship) and offering things that I’m sure his wife does not know about nor would he ever tell her. He hasn’t told her about our affair, nor would he tell her he’s helping me with surgery money. Isn’t that omission deceit already - I don’t think is kissing would be much worse?

 

He came by my job today, jovial and friendly as normal. He held my hand in front of my customers. The same man who has told me about his need to be discreet! Plus, why wouldn’t he consider that with my being in love with him, seeing him is hard for me, like dangling a piece of food to a starving child.

 

All of this makes no sense - I know I should probably cut off contact but I really also want some idea of why he’s playing all these games and saying all these things and offering all this help (that I don’t ask for) if we “just a have a friendship and kissed once”. It feels like more than just friendship on his side to me - is that fair to say? Why does he not just end things if it seems like that’d be much easier for him?

Edited February 22, 2018 by WillaLewis448
Added word for clarity of sentence