i found this helpful for myself and the OP should read it. UpV — bigbadmouse 35 secs ago

Saying I didn't stalk you says to me that you feel you need to say it and leave me wondering as to why. — Pavel 21 secs ago

Hi, pretty good answer all around and thank you for being open about yourself. I just have one question. If someone from your past popped up just as you were transitioning and said they found you through some stuff that clearly required them to dig, even if just a little, and said they just wanted to be supportive, you wouldn't be worried that they were a chaser/fetishist? It would be at least a little concerning, but I don't know how I would alleviate that. — AGirlHasNoName 8 secs ago

Hello Rakt, posts on IPS usually require a set goal to achieve and especially shouldn't be either a phrasing request or a general "How to do...?" Sort of question. So you should explain us first, what is the problem with the aproach of just telling(/writing) her what you wrote us here? And if you explained that, we would see a clear problem and from that ongoing, you could ask us how to solve the specific problem you are facing. We can't tell you how to contact that person or what to write/tell when contacting. Thats most likely why you question is closed already. — dhein 1 min ago

@dhein Thanks for your comment. I have abridged my long question and made the problem more objective. Could you point out exactly where I need to improve in this question at this point? I will try to refine it further tomorrow, as I am travelling right now. — Rakt 1 min ago

Where are the parents of that child? — Taladris 58 secs ago

One caveat to this. If she knew OP pre-transition, not acknowledging the transition may make her afraid respond lest she alienate yet another person in her life. Thus, I think it would be prudent in this case to mention it somehow. — bvoyelr 2 mins ago

Are the doorbells labelled at all, or could they be? — Upper_Case 2 mins ago

Many people are stupid (to some degree) and stupid people make stupid jokes about transgender people who are not present. These people may behave a lot better if the transgender person is one of them (and be a bit ashamed of their stupid jokes). Now if someone is hostile, that's different. They will be hostile to a colleague who turns out transgender as well. I hope I'm not too optimistic here. — gnasher729 1 min ago

"If the method by which you obtained her contact details inevitably resulted in you finding out she transitioned..." Well, it resulted in finding out she now has a female name instead of a male name. So if OP finds out that this is definitely the same person, then the female name should be used, whether transitioned or not. — gnasher729 1 min ago

@perilousGourd: Since it's hard to gauge for me, if I wasn't hundred percent sure it was the right person, how would you feel about someone asking "Hi Matthew, I knew a Matilda Smith at school, was that you?" and never mentioning the old name again? — gnasher729 38 secs ago

@gnasher729 Ya... One of the fortunate/unfortunate things about being in the closet is you have the opportunity to learn just what kind of stupid some people are. — apaul 1 min ago

@Upper_Case : Reading between the lines, "I want to be able to open up" shows an urge, and "provides valuable insight into who I am" is another reason. — ankii 2 mins ago

Can I offer two more options: asking her if you can visit (or perhaps offering to visit, these are very close to the same), or showing up to visit but being emotionally prepared to leave if it turns out to be a family moment and you're intruding? It's not just visit-or-not, there are shades to this. — Kate Gregory 1 min ago

Not to sound insensitive, but have you confirmed that she has been in the ICU or hospital or are these things she told you? Because, just taken from what you've told me, it sounds like she might be dodging you. — Joe-You-Know 2 mins ago

@Joe-You-Know Not on the ICU part, but the first time she went to the hospital she sent me a photo from her bed there. I did ask if she still wants me to visit tonight but haven't received a reply yet. I said it would be okay if the answer is no. Her family was visiting her yesterday evening (why she said to try Tuesday instead), so I assume they are still there. She already met my brother- the impromptu date I had plans with him before we met there so he tagged along the first part then gave us space. — EngineerInLove 20 secs ago

Sorry part of that last should have been directed at Kate. I'm just freaking out a bit and not sure what to do. I want to be supportive, but worry about getting too close too fast. Before this I've been on maybe 3 dates in 10+ years. — EngineerInLove 1 min ago

@EngineerInLove, okay, that makes things a little clearer. — Joe-You-Know 1 min ago

Well, this isn't really an interpersonal skill. You don't ask how to check with her if visiting is ok, or what to say and do if her family act like you're intruding, or how to explain to her or them why you want to visit. It's more "what to do" which is off topic here. Personally, I would show up. Showing up is almost always right, all the more so if you can go away gracefully if it's not right. — Kate Gregory 2 mins ago

I like this idea. You hit it right on the head, the timing just isn't good and I don't want to add stress. I mean well but am somewhat clueless when it comes to this stuff. She offered me an out after missed date #2, said she'd lost friends, etc over the health troubles and it was alright if I wanted to drop off but she's still interested (her words, not mine, but paraphrased). My initial response was that if you care about someone you try to be there for them. I really don't want to add stress. You're right, I need to back off. Will let her know that I care but want to give her some space. — EngineerInLove 1 min ago

@ankii Both reasonable deductions, but I'm interested in a direct report from the OP since no one else can give as good a report on their preferences and intentions. The specifics on how and when the OP tries to communicate this aspect of themselves are very important to the stated goal, and (I feel) the question doesn't contain enough information for that information to be interpreted reliably enough that I would use it to inform an answer. — Upper_Case 50 secs ago

Knowing how to deal with a loved one or friend in the hospital is though. I've never had a friend in such dire straits before. Couple of relatives had short stays for planned surgeries, usually went well and I visited, but nothing where the stakes were high. — EngineerInLove 2 mins ago

I wouldn't know what to say if I visited and her folks were there. Probably something like I met her a little while ago and we're dating, she's told me about her illness and asked me to visit yesterday so I've come. Then the obvious ask if I can help. We're both educators (her currently, me formerly) so wanting to help is instinctive. If I can help just by being there, I'm willing to do it. I'm still uncertain about how I feel though. I question myself all the time and being vulnerable doesn't come naturally- it's something I've had to work on. Anyway, I think Dave is right. — EngineerInLove 2 mins ago

@ankii Both reasonable deductions, but I'm interested in a direct report from the OP since no one else can give as good a report on his preferences and intentions. The specifics on how and when the OP tries to communicate this aspect of himself are very important to the stated goal, and (I feel) the question doesn't contain enough information for that information to be interpreted reliably enough that I would use it to inform an answer. — Upper_Case 54 secs ago

@a3nm OP being the only one with the interest is precisely the point. It makes the other person feel what OP is feeling. Perhaps they alter their behavior, but probably not, however they will now see OP as engaging them in the sort of playful manner they engaged OP in. Anyone who thinking this sort of teasing is fun/playful is unlikely to be offended when OP does it back. — Graham 22 secs ago

@gnasher729 Personally (different trans person here), I'd definitely prefer if you said something like "Hi Matthew, I think we knew each other in school" and then saying something identifying either about yourself or about your relationship that doesn't involve the name. I wouldn't particularly be offended if you said the old name in that context, but I definitely wouldn't like it – and also it only helps you remember the interaction, it gives nothing extra to the person you're talking to. — anon 1 min ago