Often, when a cis man approaches a trans woman with either romantic or sexual interest, it is met negatively by the female in question. This can even often happen when the male has 'done everything right', so to speak.
Why is this?
Well, deeper societal issues are at play, which complicates the matter.
Men who pursue trans women, are often labelled as 'chasers', by the Trans Community. But what about the guy who isn't just looking for sex, the guy who does everything by the book, is respectful, and wants a meaningful relationship with a trans female?
The problem is, We aren't respected as people by society. We aren't given rights, we are hunted and killed. The only time we are ever desirable to any part of society, it's cis men fetishising us. It's quite unwanted and hurtful to be treated so poorly except for to be fucked in secret by horny losers who would beat us if they saw us while they were with their pals.
When society accepts us as people and respects us, then perhaps the sexual attention won't be looked on so negatively.
Now, for this hypothetical male who is a 'good guy' and not a chaser: You have to make it appear you didn't seek them out or talk to them because they were trans. Should seem you happened on them like you would any other woman. And don't bring up them being trans, their gender, or their transition, unless they do first, or they've specifically stated its ok to do so.
None of this guarantees you success though.
A lot of us will NEVER be interested in cis men, because of how badly they treat trans ppl. I'd be one of those people these days. If I was on the dating scene, I'd only ever consider a trans woman, any guy who showed interest, I'd ignore.
We are going to be often biased against our oppressors. It will often take a lot for one of us to warm up to part of the group that seeks to annihilate us, abuse us , mistreat us.
Now, if you're doing everything right, and not being a slimeball, you're still going to get negative reactions. Please don't blame yourself, it's not your fault, you just have to understand we are scared and defensive and fed up.
There are so many trans women out there who need someone to love them, to care for them, and treat them right. They deserve someone good for them. Please don't be put off or scared, because of a bad experience when approaching a trans woman.
Trust me, we make great partners, even if we're a little extra work. :p