First date

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Frodo: 
Frodo wanted to take you out on a small simple date still romantic but simple. Maybe like a picnic or maybe letting you pick a date he doesnt want to make you uncomfortable by taking you somewhere that you dont want to go but for the first date you most likely went to a gathering together with the other hobbits and danced the night away together drinking and laughing. Bilbo teased the shit outta that mf when he got home ik it 

Sam: 
He did something classy. Maybe like setting up a romantic dinner in a field or his bakyard with airy lights and flowers and he did it right at sunset so you guys could watch the beautiful colors together and soon after you ate his wonderful home cooked meal, he walked you home kissing your hand

Merry: 
He is so awkward, he didnt know how to ask you or plan it at all he didnt know what you liked or if youd even like the ideas he thought of. So when he tried to ask you he completely fumbled over himself and he just asked you if you wanted to go out with him he ended up just letting you pick 

Pippin: 
He took you to a wide field and you guys talked for hours and picked flowers and made flower crowns and just layed down talking for hours, at one point you may or may not have went to farmer maggots field and took some stuff but non the less it was fun and you hung out all day 

Bilbo: 
Sweet baby invited you to his house. It wasnt anything out of the ordinary since you went their occasionally but when he said as a date you were even more ecstatic. He didnt like the idea of going out too much it meant he would have to dress up and plan and just go out and see people so when you got their you just talked and had some tea and he made some dessert. After a while of talking and eating he taught you a recipe he had for one of your favorite desserts/foods and you two made it together and you extended your stay longer than expected eating it by the fire. He then walked you home avoiding people of course and taking a long quiet way there to spend more time with you, he thanked you for your time and asked if you two could do it again sometimes with maybe a different recipe and you agreed (sorry its so long i just love him sm!) 

Legolas: 
You guys dont have much time to go on dates so instead he just waited till you two confessed your feelings and started dating to do something remotely sweet to make sure it wouldnt disrupt your schedules. And one day you walked into your room and sitting were flowers and something he knew you loved with a little note he wrote. 

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