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I posted this as a reply to my own forum from last week “Long awaited invitation.” A couple of weeks ago my wife asked me if I wanted to go to lunch dressed up and while it took a couple of tries, we finally did it last Friday. It was a great time, but also really instructive. I learned a lot about myself and feel like I overcame some important barriers. Happy to chat and share what I learned (beyond what I’ve written here) if anyone’s interested.
So, the original plan was to go to lunch on Tuesday. I got dressed and was excited to go out (but nervous), but my wife didn’t like my outfit. I’m not sharing this to complain about her, but I learned something important about getting your SO to accept this and I think this might be helpful. I bought this new dress that I really like and think looks pretty good, but my wife laughed and said I looked funny. That hurt a bit but most of all it really destroyed my confidence. We still almost went, but ended up cancelling. I really regretted it later and even now wish I had gone anyway.
After a couple of days, we decided to try again on Friday. I was able to dress up for work that day (which was really fun, it had felt so long) and when I got home she was still up for going out with me en femme. I changed into something more appropriate for a casual lunch (rather than my office attire) and off we went. After working all morning dressed up I felt a lot more confident about our lunch.
We debated about where to go and my wife ended up picking a buffet. This made things a bit trickier because I couldn’t just slide into a corner booth and go unnoticed, I had to get up and repeatedly go get a new plate for each course of the meal. The buffet, of course was situated right in the center of the restaurant and so everyone could see me every time I got up for a plate of food. I had mentally prepared myself for talking to a server, but the buffet felt like a lot bigger step.
Anyway, we went and everyone was kind. We paid up front and went in and found a seat. Our server was kind and polite as ever and nobody treated me any different than normal. We finished, left our tip and went home. On the whole, it was a pretty normal lunch. We talked about different things like we might any other time and that was pretty much it. I had a great time and am looking forward to our next lunch together. There’s a restaurant close to my office so maybe next time I dress up for work, she can meet me and my office for a lunch break.
Here are some of the things I learned from this experience:
1. Whether or not you like an outfit, if you want acceptance from your SO, you need to be sensitive to their tastes and feelings. I will still wear that dress in the future, but probably not to lunch with my wife. I’ll pick things I know my wife is more comfortable with, and that’s fine. This kind of thing is part of the compromise of being married.
2. I was nervous, but things worked out. I was much less nervous on Friday when I went than on Tuesday when I bailed. I think sometimes a false start or two is pretty normal. Don’t feel like a failure if it takes a couple of tries. I hadn’t dressed out in public in a while, so my nerves were a bit higher than usual. Going to work first and then to lunch made things a bit easier.
3. My wife and I had a great talk about the whole thing. She explained what she thought looked better on me or not and what made her more comfortable and I explained how I felt when she laughed and didn’t like my outfit. This was a good opportunity for communication between us. Successful relationships are built on communication, and this was overall a great moment in our marriage.
4. People noticed me. I could see them looking at me. I think I heard a bit of laughter too, but that’s ok. It was still fun, and I look forward to doing it again. I saw one lady eyeing me especially hard, and even whispering to her husband and pointing me out. I didn’t care, I just smiled at her and laughed. I wanted to send the message, “yeah, I know I look a bit weird, but I’m having fun, it’s ok if you stare a bit.” When I first started dressing up, I wanted to pass so badly. I thought I could never go out if I didn’t pass perfectly. I realize that probably isn’t going to happen now, but I can still enjoy the experience. It’s ok if I can only ever be a guy in a dress. Brina McTavish wrote recently about the importance of self acceptance, and my ability to do this was strengthened by this outing.
5. Upon reflection, I always wonder how many people really looked or cared, and whether or not my feeling that they paid more attention to me might just come from the fact that I was more sensitive because of nerves. When you’re dressed up, there’s a temptation to think that every snicker, laugh, or stare is about you. When we’re nervous or scared, small things can seem bigger and worse than they are. If you’re scared and nervous and feel like everyone’s looking at you, remember that it’s probably really just your nerves more than anything else. Relax a bit and just enjoy the weirdness.Oh, and for anyone wondering, I worse a pair of dark blue skinny jeans, a black mock neck top, with a light grade cardigan and a pair of 2 inch chunky heels that are comfortable and work in both work and casual settings. I had my usual brown wig on done up with a hair clip in the back.
Sarah,
This sounds like a fairy tail to me. I dream of lunch or shopping with my wife. We have talked about it but haven’t made plans yet. It may be a while before the chance to do so comes around. When I’ve went out in the past I too worry about passing and being perfect. Any laugh or whisper makes you paranoid. One of the last times I went out two guys laughed and pointed and hurt my confidence. Since then I’ve worked on clothes and makeup to help my look. But im still a but scared to go out but I really want to.
The last time I was at the store dressed up I heard a guy say, “Is that a boy or a girl?” I actually don’t even know if he was talking about me, but I assume he was. It was awkward at the time and I wanted to get away, but after I thought about it, I realized that I should have just smiled and laughed. I think part of self acceptance, in anything, is letting go of approval from others. Even if I will never look the way I really would like to, even if I can’t pass, it’s still fun to dress up. Learning to enjoy things, regardless of what others think, or how well you do them, can be a really powerful part of life. This is one of the things that cross dressing has helped me with, learning to enjoy something, even if I’m not very good at it.
Good point, Sarah. I recall one similar situation. I was touring a museum and I (surprisingly) overheard a guy asking his companion if I was a woman or a man. I took it as a positive, since I figured I was too obviously male! Having them guessing was a step in the right direction!
Sounds like it was a wonderful experience – both the outing and the lessons learned.
When I go out, I always have that same question in my mind: Are they seeing a woman or a guy in a dress? My dear Sister Friends have assured me that it doesn’t matter what others think, it matters how I feel. If I feel confident, all is good.
I manage to get out at least once a week and have grown more confident and comfortable with each trip. Oh, and a Breakfast Buffet place has become my favorite Saturday morning eattery. The staff has been VERY accepting and wonderful.
Sarah, you have a wonderful wife, who only criticized your look to let you know that it wasn’t something that could work to at least try to blend in while you were out with her. I’m trying to understand her viewpoint, and she doesn’t want to be seen with her crossdressing friend, she wants to be seen with her woman friend, and that’s likely just what she helped you achieve. Count your blessings, and give your wife a big hug for helping you out. You are very lucky.
Thanks for the follow-up, Sarah!
I think it all turned out rather well. Most importantly, your wife was comfortable and able both relax and talk freely about her perspectives. She seems wonderfully supportive.
I am curious about your work situation. I gather that you routinely dress for work. Apparently that is working out well. Could you shed some light on your process for coming out at work?
Hey Kim,
So, I wrote an article about this here on CDH. There isn’t really a lot to tell, actually. I work at a university in a very open minded department. So, I decided to dress up for work. The first day I came in, I think no one even saw me. It was during COVID and a lot of people were working from home. Later, a few people saw me and so over time gradually it got to where everyone in the department had seen me dressed up. I’m not trans, so coming into work isn’t a daily thing. The last couple of semesters I haven’t been able to dress up as much, but once or twice a week is kind of my goal.
I’ve written about this a few times in different forums, but one of my best experiences was getting locked out of my office and having to find the secretary to let me back in. At the time I shared office space with another person who was meeting with a student and needed a bit more privacy. I went down to the computer lab to keep working and came back after the hour my office-mate needed, but she was gone and I’d left my purse and keys inside. I didn’t even have my phone to call. Normally it’s not a problem because the secretary has extra keys, but she wasn’t there. No one else was in the department at the time so I had to hunt a bit around campus to find everyone. Turns out everyone was out on the lawn at a university wide corn-hole tournament. It was fun because I got to take my spiked heels off and walk barefoot across the grass to where everyone was hanging out. Anyway, long story short I got to spend more time than expected dressed up, and got to range further away from my office than I normally would, and walking barefoot across the grass, carrying my heels, felt oh so sexy!I have to say, for a non trans person you are enjoying a pretty great coming out experience!
Sarah –
Thank you for sharing your experience. It is wonderful that your wife is so accepting that she went to lunch with you. The outfit you wore sounds lovely. I wish you more opportunities to enjoy outings in the future. It is nice that you are able to dress for work on occasion. Thank you for sharing your experience on getting locked out of the office.
XOXO
SuzanneCongratulations! It was a huge step for me to tell my wife but more importantly was her support and acceptance. For my wife it doesn’t mean she’s all the way there yet but we now have great conversations and do things like you are doing.
I could tell in the way you shared your story in how much that has meant to you. A simple thing like lunch and to be able to talk about life and the things related to you being you is so fulfilling …feeds your soul and heart .
Im very happy for you and thank you for sharing your joy!
❤️ Carole
I think the best part, in an odd kind of way, was that it just felt pretty normal. I mean, dressing up is always a bit of an adventure, but I was grateful for the fact that my wife and I could go out together without the fear and worry we’d felt before. I think both of us are moving along in positive ways. I’m looking forward to our next outing!
Once it starts feeling completely normal, you know you have moved on to the next step in your journey. For me, it started feeling more normal very quickly after my first 7 or 8 times out in public. Since then I can’t tell you how many times I’ve been out and about doing whatever, looked down and was surprised to find I was wearing a skirt or a dress.
Sarah, I loved every word of this! You didn’t just go out, you let the world in, too. Whether with your wife’s reaction to your first outfit or the buffet style restaurant or one person eyeing you who can’t let it go, you made a positive outcome for yourself by handling each moment of uncertainty with poise and composure. I really admire that! Jill
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