I'm not sure if I can still send this ask. Please ignore this if you're not still open.
What would the boys do when they see a good friend/SO hugging themselves because they're sad? Or a friend/SO who they've never seen cry and know for a fact they don't cry easily reached out to them for a shoulder to cry on.
Friend, SO, or whatever you find more fun.
If you're looking for more of a fluffy answer then S/O is the way to go so I'll use that.
Sans - He tries to make you laugh. It's his go-to if he can. Sans can be awkward around certain emotions and he thinks he fumbles but he's actually very comforting to be around.
Papyrus - Gives you a hug. The best cure for the sads is a Papyrus hug!
Blue - Is his chipper self as he helps you work through your emotions. He'll help you work out what's making you sad with enthusiasm and positivity which will have you feeling better in no time.
Stretch - Probably the best and worst person to go to for this kind of thing. On one hand, he'll probably stick his foot in his mouth but on the other, he's incredibly comforting. Stretch has a warmth to him that many of the others don't possess and it's always nice to be around.
Red - Also probably the worst person to go to for this. Red's awkward with emotions on a good day but now you're crying and he has no idea what to say or do so he starts patting your head in an attempt to make it better while telling you in a hushed tone to cut the waterworks. If you look at him though, he's blushing.
Edge - Not the warmest guy in the world, but he does know how to listen. Edge will listen to what's making you upset and offer solutions to your problems. When it's all over, he'll brush back your hair (if it's long), kiss your forehead and move on with his day.
Vi - Tells you to tell him what's wrong. He'll help if he can but he can't if you only cry. While Vi can flip-flop between warm and cold, he's a good person to talk to when sad. He's gentler then.
Money - Like Sans, he's gonna do his best to make you laugh and forget your troubles. Money's excellent at it too. It's hard not to laugh at this goof.
Black - Just sits there with you and hums. He doesn't say anything or tell you to tell him what's wrong. Black just continues with his work but he'll hum to you to calm you.
Wolf - Hugs you and then you're trapped for hours. Enjoy.
Bear - Tries to make you something to eat or he'll get you something to eat like a cookie. When he's sad, he likes to eat, so maybe you might like a treat too.
Sparrow - Like Papyrus he offers a hug right away. It's warm, comforting, and it's always just what you need.
Wine - Makes tea for you then sits down with you to get to the bottom of what's made you so sad. He'll help if he can and offer solutions to whatever it is that's affecting you.
Coffee - If you cry, he'll cry. Prepare yourself. It's just his gut reaction to anyone else crying. He doesn't mean to it just happens. He'll, of course, give you a hug but in the end, it sort of just turns into you soothing him. For some reason though, that helps you feel better.
