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Looking at the updates, I'm trying to have a threesome with Bernard and Caleb. It says I need to have Bernard on 4 hearts and Caleb on 1. I can;t get Bernard past 3 hearts for some reason. It says something about fun with Caleb but no matter what I do, I can't find that option. Also, how do you have sex with Logan? I'm on his normal route.

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Oh you are talking about the 3.3 update. I deleted my response for the 3.2 update. 

You can get 4 hearts with Bernard by watching fireworks with him. 

I am working from memory here (I nuked my saves for the update) but I believe "Fun with Caleb" appears in Bernard's talk menu when you visit him at night. You have to have talked to Caleb about Bernard first for it to show up. I know there is a trigger to go spend the night with Caleb in Bernard's talk menu for sure. If I'm right and you do that once, "Sex with Caleb" should show up another night as an alternative to "Fun with Caleb". After you get the 4th heart.

Normal Logan's one-time sex scene is the "I owe you a beer" Event. From the Dev log:

Event: ‘I owe you a beer’ - entering your new home (Req: Evening, Bareshade's Expansion event completed, Ste’s New Farm Road completed, ‘Clash with Barrel’ seen, ‘Ask about his work’ done with helping, Like 40, Love 1)

‘I owe you a beer’ event have four variants (Normal, Top, Bottom/Vers with high WW like and without it). Doing anything but normal is your own risk.

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I've talked to Caleb about everything, but I don't recall much about Bernard other than asking him about his best friend and stuff. There was never any Fun with Caleb in Bernard's Talk menu, only ever Night with Caleb, which is weird.

NIGHT WITH CALEB, that was it. My bad. OK I am gonna run through fast as I can and try and see, but my hunch is you need the 4th star to unlock both Fun with and Sex with Caleb. Get the star and check both their talk menus, best advice I got atm.

Ok, fun with Caleb happened after I clicked Night with Caleb, and it was the alternative to sleeping. Sex with Caleb isn't appearing. I've spoken to both during the day and there are no options that aren't normally there. This is annoying lol. I do have Bernie on 4 hearts tho

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Did you speak to Bernard at night? And congrats on getting that far!

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Yeah. Three times now I've spoken to him at night and each time it just says Night with Caleb. I do it, and then we go to the barn and im given the option for fun or sleep and that's all

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OK I am gonna try and power through but it's gonna be a couple days at least. I'll keep you posted.

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Thanks!

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Do you have 1 heart with Caleb yet? I can't remember if it's from the fireworks or from giving him a treat (both new options in the Patreon version).
The option to talk to Bernard about you having sex with Caleb is in his talk menu during the day in the shop, not in his home at night.
Admit to Bernard that you've had sex with Caleb,  then that night suggest you two spend the night with Caleb, it will start off the same as usual, but then once you 3 bed down for the night the scene will diverge.

Thank you.

Yes, I did all that. However when I choose to go at night, the only options are fun and sleep, no sex. The fun that happens is usually a threesome of sorts, but its not what i was expecting.

So after getting the heart with Caleb, admitting to Bernard during the day that you had sex with Caleb, and then taking the usual picnic to the barn at night, you didn't end up with an oral 3some?