He played it safe, and now it’s going to blow up in his face.
At least he will have the memory of one blissful afternoon of paying for Hannah’s Fro-Yo to sustain him during the inevitable darkness.
If I outed myself on casual dates then I’d worry about my ability to stay stealth and I would worry that the person’s preconceived notions about trans people would alter their view of me, likely seeing me solely as a trans person before they see me as myself.
Long ago, in the days of my teenagehood, I took a chance and played Shiritsu Justice Gakuen: Legion of Heroes, the import version of Rival Schools: United by Fate for Play Station. I stumbled through it like a good import fan should.
Stealth Attraction was the first course that got me to pay more attention to Richard La Ruina.
Caveat: These techniques are only for men of intermediate or advanced level who already have pretty good image, fashion, fitness and attraction skills.
If you're a beginner there's a risk they'll do more damage than good.
stealth date: when a male friend asks a female friend for a one-on-one outing, during which he tries to exert date-like behavior such as paying for the food/activity, going somewhere non-casual, or making exceptional plans for the outing, all the while never specifying that he wants it to be a date.
Over at Boundless in an article entitled “Help, I’m on a Date and I Can’t Get Out!