Ashley, I really like hearing your story. I look forward to hearing more! Topics I hope you cover – feelings/emotions towards self (earlier in life & now), dating, telling other people, especially family.

Looking forward to more of these! This starts out slow, but for your first one it’s really solid. It looks and sounds fine. Once your friendship starts showing the pacing picks up well. I agree with Kim, the question and answer format is excellent.

Ashley, I’d be curious if you remember what that initial advice from that first call to the transgender support line was (before you decided to follow up with calling that cellphone number).

One thing that feels really different about this is how early in your process you’re sharing. Partly, I’m sure, it’s the first podcast and thus a little tentative for that reason, but I don’t think a lot of folks would have realized just how gradual a process this can be. Your question to yourself about “Would I be mad at myself 10 years from now if I don’t do something?” packs a real wallop, particularly with the knowledge that you’d already gone almost 20 without embracing this side of yourself.

My prior experiences have either been people who are very clearly strongly driven to be publicly the other gender or else men for whom dressing female is a very sexual thing and not necessarily tied up with full-time gender identity. Though, now I think about it, I am guessing I’ve met a wide range from actually transgender to post-gender to play-time-gender-switching. Ah, San Francisco living…

When you’re comfortable it would be really interesting to hear about your experience with clothing that is perceived as feminine or female. I’m guessing you might have had to go through some sorting out of “Is this about what turns me on or about who I am to the world?” when you first began to think about crossing some traditional gender lines and looked around to see who else does that. Which makes me wonder what you’ve thought at different times as you’ve seen men dressing in women’s clothing. There’s a big range out there from the ridiculous (e.g. Monty Python’s pepperpots and Big Mama) to fairly sensitive character acting (e.g. some of Dave Foley’s female characters on Kids in the Hall) to the matter-of-fact (e.g. Eddie Izzard) to full trans characters (e.g. Crying Game).