Dating Advice

Hi @Jaila 

I don't have any advice relating to your specific situation, but I just wanted to jump in and say good on you for wanting to put yourself out there after being in such a long term relationship!

I broke up with my partner of 12 years about 5 years ago now and had no idea what to do with myself at the time, so I really respect the clear mindset you have.

Are you interested in pursuing something more with your gentleman friend?

Warm regards

SkySeeker22

Hi, @SkySeeker22 ,

I’m of two minds over this gentleman.  We’ve been friends since a chance encounter 4 years ago.  I was selling my kayak, he was buying one.

He’s a fabulous guy, takes me out occasionally, spoiling me with fine restaurants and great conversation.  This weekend we are going to a 5 course tasting dinner and a 5 course wine tasting.  Very posh. He’s attentive and funny as well.  He lives a good 90 minutes from me however, so it’s not frequent.

He, unfortunately, knows nothing of my past, only my current break up and the problems I am having adjusting to a new, fairly complicated home life.

I think seriously pursuing him could possibly be a mistake since I’m still recovering from the most life shattering experience of my life.  But, on the other hand, he seems a near perfect fit and I’d hate to lose him because of a stupid misstep on my part.

So, I suppose I’m asking for advice in two areas:

1. How to move forward with him

2. How to meet people in my area that aren’t afraid to be with a trans woman.

Hi again @Jaila 

It sounds like he has been in your life for quite a while then! Would you feel comfortable in opening up to him and just explain your two minds about the situation?

Warm regards

SkySeeker22 

Well, how does one actually have that conversation?  I mean, the last time I actually had that conversation was many many years ago with the end result of being disowned by my entire family for nearly 30 years!  Obviously, that didn’t go well.

Besides, I’m not even certain his intentions are anything beyond the friendship we have now.

Do I just “let it slip” in conversation, or do I approach it head on with no preamble?

Hi@Jaila

I'm hesitant to offer any dating/relationship advice to anyone... as someone who is as bad at it as i have been, just be wary of listening to anything I say.

I tend to think if there's any chance of a long term relationship with this man, then anything he is going to know about you and your history eventually then you might as well talk to him about it now.  If anything changes the way he feels about you then better to find out now.  And if he knows you're feeling a bit hesitant over taking things further right now because you're still recovering from the last breakup, you may find out that he is very supportive and happy to take things at a pace you're comfortable with.  He seems like a really understanding and caring person.  That's my 2c worth anyway.  I hope it works out well for you.

It’s funny, because it’s not like I’ve intentionally left anything unsaid so far.  It’s just that being trans hasn’t been an issue I’ve had to deal with on a day to day basis.  It just doesn’t come up.

No one has known unless I’ve specifically told them.  Even my psychologist was shocked when I told her.  She’s helping me get thru the depression I’ve been experiencing in recent months. (Intentionally left my job to find a new one, the the breakup the following week, then my mum’s diagnosis of cancer the following week and her death the week after)

But, I do agree in principle @MJG017.  I don’t like it being left unsaid because it is a big part of who I am and will eventually come out.  If I don’t eventually breech the subject, I’d feel terrible because I’d feel like I’m hiding an important side of my life!

But how?

@Jaila 

I'm sorry to hear about you mum.  It must have been such a shock and then to lose her so quickly.  I've been dealing with cancer for a couple of years now so I know how hard it is on everyone, but losing her so quickly after the diagnosis must have been so terrible.

I remember when I first tried dating in my early 40s... yep, I did say I was bad at it... there were so many things I thought I should hide about myself because it would just reduce my chances too much I thought.  Now I don't want to in any way compare what I felt any potential date wouldn't like about me to what it must be like as a trans person.  I don't have any experience in that area at all, but I can see how it could be a big thing to tell someone if they're not aware.  I honestly don't know how I would handle that if it was me having to make that decision.  But I ended up going with as honest as I could for 2 reasons.  To avoid an awkward conversation if things started going well, and if they agreed to meet me then they already knew those things about me. If it was a reason to not go out with me, then it was never going to work anyway I thoughts, so might as well save both of us that time.

As you say, it is a big part of who you are, and I can tell you're not trying to hide anything, but I also understand the hesitancy when you both seem to really get on well at the moment.  But I just think it's one of those things that the longer it goes without you bringing it up, the harder it will get.

As for the how?  That's difficult.  I'm not being very helpful am I.  I suppose you could just say there's something important you need to tell him about yourself and that you do trust him enough to tell him and that it isn't easy for you.  Whatever you decide to do, I really hope it works out well for you.  It does sound like to me that you know you want to tell him, but obviously don't want to risk what you have with him now.  All I can think of to add, is that if he's what you see in him, then his response will at the very least be respectful to you, so trust him to be the type of man you feel that he is.

Thanks, @MJG017 for your advice.

I think I will brooch the subject with him this weekend.  We have a very nice day planned together, but it’s important to me to be 100% honest with him.

After dinner, when we are in a more private setting, I will bring it up.  And, I think I will use your approach.  

He’s been a great emotional support for me as I navigate the legal complexities of my divorce/permanent separation, whatever you call it. I want to be 100% open with him because I value his friendship and compassion more than he can know.  And from there, I’ll just explain why everything has hit me so hard these past months, working in some of the explanations my therapist has given me.

I don’t want to lose him, but I can’t completely hid my background in cases like this.

That being said, if things do go asunder, I still need to move on.  So, how does a trans woman find true companionship in todays world?

Ill keep my fingers crossed for you for the weekend @Jaila Hopefully the 2nd question wont need an answer.  The thing that worked for me was dating sites, but they're predatory with their pricing, free ones are full of fake profiles but at keast you can be open and honest from rhe very start and only try dating with people who accept us based on all the info on our profiles.  Im not sure i could face doing it all again though.  Hopefully though this is a question that you wont be needing an answer for just yet

Unfortunately, while at work this evening, I learned the he has had to postpone our date this weekend until the following weekend. ☹️

I'm a bit disappointed to say the least.  Been looking forward to this for two weeks.  Sigh.