The "Trophy Waifu" and "Get Over Here" achievements seem to be bugged, and can't be unlocked.
Edit: It seems that i just had to close and reopen the game for Trophy Waifu to activate. This also happened with Shopping Spree, before. Get Over Here still hasn't unlocked, so I'm either misunderstanding the goal of it or it's actually bugged.
First of all, mad dedication bro. I would not have that kind of perseverance for a single achievement.
Anyways, I managed to get all the achievements recently and had this problem with a few of them. Restarting the game and keeping track of my catches worked eventually for "Get Over Here", but if all else fails you could try making a backup of your current save, deleting the game, and then redownloading with your loaded backup (the save is in AppData > LocalLow > HotPink and Annue > Tentacle Locker 2. Grab the TL2 folder and save it somewhere that isn't in AppData, then put it back after you redownload).