Nervousness is very common. They are often worried about how their date will react to their crossdressing. For example, they might be afraid of being judged or rejected.
One crossdresser I know had a first date at a coffee shop. They were really nervous but decided to be true to themselves. They wore a beautiful dress. Their date was a bit surprised at first but then they started having a great conversation about fashion and self - expression. It turned out to be a really positive experience.
One story could be about a teen crossdresser who, while exploring their identity, had a very unique first time at a school event. They dressed up in their crossdressing style and received a lot of positive reactions from their closest friends which boosted their confidence.
My friend had a first date at a park. They were sitting on a bench having a nice conversation when a huge gust of wind blew by. It blew my friend's hat right into a nearby pond. His date found it hilarious and they ended up spending the rest of the date trying to fish the hat out with a stick.
One time, my friend was on a first date at a really nice restaurant. They had eaten some beans earlier without realizing. Mid - conversation, a small but audible fart slipped out. They were mortified, but their date just laughed it off and said it was no big deal. It was so embarrassing for my friend at first, but in the end, it actually made the date more relaxed.
Crossdressers can communicate their feelings through honest conversation. They can start by sharing their insecurities and hopes for the sexual experience. For example, they might say how they feel about their appearance in the crossdressed state.
There are stories where crossdressers in gay relationships contribute to a more vibrant and inclusive relationship. Their crossdressing can add an element of creativity and playfulness. For example, they might plan themed dates where the crossdressing is part of the theme. This not only makes their relationship more interesting but also helps them to better understand and appreciate different aspects of gender and identity, and it can strengthen the bond between them in a very unique way.
In case it smells really bad, you could excuse yourself and go to the bathroom. Spray some perfume or something when you come back. Then, when you return, change the topic to something more interesting to distract from the incident.
Well, one common thing that could go wrong is bad communication. For example, if one person just talks about themselves the whole time without showing any interest in the other. Another is having really different expectations for the date, like one thinking it's a casual coffee meet and the other expecting a fancy dinner. And sometimes, personal hygiene can be an issue. If someone shows up looking unkempt or smelling bad, that can definitely make the date awful.