To most women, whether married or not, spending some time with a girlfriend who is feeling alone and depressed would be a perfectly normal thing to do. Until the past week or so, I'd never considered this in relation to me being the supportive friend.
When I used to get really depressed (sometimes to an almost-suicidal extent), I suffered alone. While I'm not entirely over depression and probably won't ever be, two things helped me. One was coming out as a crossdresser, which took away a lot of pressure to conform to a masculine stereotype and hide my feminine traits. The second was that I discovered that I am chemically sensitive to the artificial sweetener aspartame, which caused or exacerbated a range of problems for me, including skin rashes, heart palpitations and a fog-like blanket of chemically induced depression.
Having lived through such bad depression, I understand it well enough to empathise with other people who are suffering through it, and to want to help where I can. In fact, that's one of the things that drives me to continue attending the cafe nights regularly. I know that closeted crossdressers are prone to depression and I want to help to provide a path for those who want to come out of the closet because I know that it will also help in dealing with depression.
A few years ago when I was still mostly closeted, one of my nieces attempted suicide and ended up in hospital for several months. She was later diagnosed with a mental illness, and for reasons closely related to that, she isolated herself from her mother while she was in hospital. Knowing that she was depressed and feeling alone, I organised around my work, my wife and my son to visit my niece in hospital most days over those months. I mostly went alone but a few times my son went with me. As a close relative, there was never any suggestion of impropriety in my visiting her frequently. We became quite close over those months, and I came out to her while she was in hospital.
I've now found myself in an interesting situation with a female friend who I met online. She is in her 20s and knows about me including my family and my crossdressing. We have met in person a couple of times when I have been out en femme, but she has never met me as a male. While I don't know all of the details, I know that she is quite depressed at the moment and is feeling rather alone. I have offered to spend some time with her because I believe that she needs a sympathetic friend.
I mentioned the situation to one of my crossdressing friends, who thought that it meant that I would be having an affair with this young woman. While I didn't think that anything like that was ever going to happen, I could see that that could easily be the way other people might see it. I discussed it with my wife, and explained the situation as I saw it, and my crossdressing friend's take on it. I think that my wife actually understands me quite well. She had me confirm that I had only ever met my friend "as Alice", and that if I did spend time with my friend, that I would be doing so "as Alice", then confirmed that she didn't see a problem. She understands that, as Alice, I am sexually disinterested. Even as a male, I'm monogamous and committed to our marriage. To be honest, I couldn't be bothered having an affair!
A little while after talking to my wife about it, I realised that I actually see my young friend as being very much like my nieces. She is a similar age, and in a lot of ways I probably consider her to be a foster niece, if that makes sense. In that context, I don't think that there would be any impropriety regardless of whether I was a foster aunt or a foster uncle.