I've seen a lot of posts about Batman using his Bruce Wayne alter ego for the good of Gotham: job programs for felons released from prison, orphanages, charities, high wages for his employees, ethical business practices...the legendary post where Bruce Wayne goes to Wal-Mart.
Thus far I've never personally seen anybody really dig into the persona of Bruce Wayne the Billionaire Playboy. A handsome, rich, powerful man who always is seen at fancy galas, art openings, charity dinners, and wild parties with at least one beautiful woman on his arm.
We know Bruce Wayne is the mask, and its Batman who has a...complex love life, depending on the iteration we're talking about. Talia, Catwoman, sometimes Wonder Woman.
Bruce Wayne's dates, on the other hand, are all "normal" people. Maybe they're an aspiring actress, a supermodel, a prima ballerina, the occasional reporter...and every time there's that bit of nervousness at the start.
Sure everyone knows Bruce Wayne. Everyone knows the story with him. Sometimes his wilder parties make the news, but there's never really been anything nasty reported about him. Never...allegations. But he's a billionaire. He's one of the most powerful people in the whole city, nevermind the country. If he did have some skeletons in his closet. Well. Men with power have a way of making those kinds of stories go away, don't they?
As time goes on the Date's fears dissipate pretty quickly. Bruce Wayne is nothing but polite, kind, and at times charmingly awkward in an 'raised by his butler in a mansion' kind of way with his dates. Some of them can tell he's holding back, of course. Maybe the more perceptive Dates notice he's smarter than he lets on - playing the himbo or hamming up the "no-nothing rich boy" act to the cameras or some of his wealthy peers.
He also listens, is the thing. He's always listening to what they're saying, is interested in hearing about their careers, their hobbies, their lives. Really listens, too. Might refer to something a Date said weeks later off-hand. Buy out the whole museum for a private dinner date with a famous painting from an obscure artist they like, or a private performance with another's favorite band.
He has anecdotes and funny stories for days that somehow says very little about his personal life. The Dates know he has kids (it's practically a running gag in the news that Bruce Wayne has adopted yet another orphan) and maybe she might spot one of them at the mansion, but Bruce seems very keen to shelter them from any intense spotlight and scrutiny, and they all seem happy if a bit weird like him.
Eventually, there's drifting. He's a very busy man, with a very busy schedule. On more than on occasion his nice old butler will call and extend apologies that Mr. Wayne will not be able to make it this evening. Sometimes it's virtually impossible to get a hold of him over the phone. After a while they stop trying. None of them feel quite surprised by that. In the end, it just doesn't work. Sure, he's a little distant and doesn't make himself emotionally available...but he's not a bad person.
Especially when the so-called "exes" of Bruce Wayne start networking. Gotham isn't a small city, but the social circles Bruce Wayne travels in aren't as big. They don't quite gossip or complain about him. More like...who else would get it?
(I touched his side once and he winced...like he'd been hurt real bad there. He laughed and said it was tackle polo. How does that even-?)
(Somehow, after two dates, he saw right through me and listened while I told him what that casting director tried to do. He nodded, gave me the contact details of a law firm, and said not to worry about the legal fees.)
(I don't know for sure it was him, but it can't be a coincidence that my building got bought out from under my shitty landlord and we were all able to buy our apartments under market value.)
(He got my brother in the best rehab program in the city after his relapse. It probably saved his life. We'd stopped dating months ago, I still don't know how he found out.)
(He gave me a card with a phone number and told me that if I was ever in trouble to call it. Said one of his cars would come to pick me up, any time, any place, no questions asked. The one time I did have to use it after a bad party, it was Alfred.)
I think any tabloid reporter digging around for salacious stories or dirt about Bruce Wayne's love life would be completely and politely stonewalled when they try asking his former Dates. Even when money is offered. Every single one of them.
