My partner doesn't mind me dressing up and actually encourages me to express myself (just not around our young son), but they don't find me attractive in girl mode; as that's not part of they're sexual orientation. Also they don't want me to shave my face as they say it'll make me look too young (I'm 30 and cursed/blessed with baby-face), and I find makeup scary to approach. They've been such a big help though with me expressing myself, but going outside, and being dressed up in front of my family is still something I haven't done. How should I go about navigating my situation?
So just so we're on the same page (or at least you know how I am interpreting your question), it sounds like you like to dress up (which is always fun) but makeup and shaving your face isn't in your future (at least for now) and you are wondering how to wear girl clothes around your family and in the real world.
When it comes to your family, the first thing is to be prepared for the normal questions, which will likely be:
-What is your sexual orientation?
-Are you going to transition?
-Are you transgender?
At a minimum, be prepared to be asked those questions. Of course, being prepared to be asked those questions is not the same thing as being prepared to answer those questions. Telling someone "I don't know yet" is a perfectly acceptable and honest response to a question you are not sure or are not prepared to answer.
People tend to associate "girl clothes" with "being attracted to men". So, if your partner identifies as a woman, then questions about your sexual preference are very likely to come up. I don't believe that what someone wears has anything to do with who someone is attracted to, but not everyone thinks too deeply about gender identity and people tend to assume that someone who wears clothes that are usually thought of being meant for a different gender probably isn't straight. The idea that gender presentation/gender identity and sexuality are connected has always baffled me but I try to be patient when I am asked this question.
When it comes to being asked about transitioning, gender is almost presented as binary, either male or female. Nonbinary people are slowlllllllllly gaining some representation in movies and television shows, but this representation tends to show a nonbinary person as someone who has, in the process of, or will transition. A nonbinary person who does not wish to transition is not often represented so that concept is pretty new to a lot of people. If you aren't sure where your journey is headed, it's perfectly okay to say that you're not sure about whether or not that is the right step for you.
Finally, when it comes to the T Word, it's up to you how you identify, if you chose to identify as anything at all. I identify as transgender, but I am not going to transition. Transgender doesn't always mean transitioning. Perhaps you identify as gender fluid or as a crossdresser or as nonbinary. Again, even if you don't know how you identify, be prepared to be asked this.
Beyond this, you know your family better than I do. You probably have a better idea how they might react. Maybe they will ask you a million questions, maybe a family member will come out to you when you do, maybe your family will shun you. It's up to you how you share this side of you with others. Perhaps you send an email to your family ahead of time, perhaps you just show up at the next family function in a skirt. All I can tell you is be patient with how they react, be gentle, and, I hate to say this, but be prepared for the worst. You need to protect your heart more than you need the acceptance of others.
Also, they may not understand this side of you. Which is fair. I honestly think that understanding is a lot to ask of someone else. A lot of people don't really wonder if the clothes they are wearing are in sync with how they feel about themselves. Understanding typically requires relatability and if someone can't relate to you in terms of how you feel about gender identity and gender presentation, then understanding becomes a lot more difficult. My wife doesn't understand any of this, lol, but she accepts me and loves me and knows this is who I am.
Listen, this is harsh but the people in our lives are under no obligation to accept us. Gender identity can be a deal-breaker for some people as they may not "approve of your lifestyle" or whatever. You mentioned having a young son, they may be concerned whether you are fit to be a parent. Your family is also under no obligation to keep this side of a secret (if that's what you want). They may choose to tell everyone about this side of you, including your kid.
My suggestion is to take things slowly, come out to your family one or two members at a time. Test the waters, if you will. Just keep in mind that this bell cannot be unrung. I encourage you to be who you are and to follow your heart, but again, you need to protect it.
As for the rest of the world, I feel it's a little easier. The world is filled with billions of people you do not know and you will never see again. Who cares what they think of you? You probably will never know what they think as you strut through the mall in stilettos with a French manicure.
Love, Hannah
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