So I missed my chance with Piper when my big moment came up since my "Romance" button was red, I didn't take it, and thus I began to pursue Curie as a backup.

Well after getting my quest done with turning Curie into a real girl I brought her around to show off to Piper, and lo and behold, Piper wanted to talk to me about something, and yes gave me another shot at her.

Was it jealousy over my new six-bot that set Piper off or was it something else?

So buck up campers, if you miss your chance for romance, it won't be your last chance necessarily.

Still unknown is if you hit the Romance button and fail the first time whether this can still happen or not.

I failed at least 4 times with Piper before she finally saw sense and fell madly in love with me. Must have been my new suit

So you didn't fail the 'check', you just never selected it. I wonder if it's different if you select but actually fail because you forgot to dress up in like a freaking clown for the CHR bonuses?

I was sure I ruined my big chance with Piper and travelled with Cait after that. Until shortly after, came across her in Diamond City. Now that I think of it, I'm not even sure why she was there, as I don't think you can send her there? She said the line about sooo, all this about being my best friend since, something like that and she's been with me ever since. Though I'm currently doing the other companion quests so I won't have to dismiss her anymore.

As far as I can tell, you only get one shot at Magnolia.

No I selected the romance and was told in no uncertain terms that she only wanted to be friends, so with Piper at least you seem to get multiple shots at it.

Psssh dress up like a clown? Those clean suits are fresh. Don't know what you're talking about. I always got the blue one.

I wouldn't mind getting the lovers embrace perk, but I'm not going to sink points into Charisma just for the privilege. I'd rather survive by taking perks more likely to bring that outcome about. I like the role playing options though. Maybe I'm too much of a dungeonmaster in real RPGs to take it as seriously as it deserves.