Rachel:
You were in the choir room rehearsing for regionals when Rachel asked if she could sing something and Mr Schue agreed so she sang L.O.V.E by Nat King Cole and everyone thought she was singing to Finn since they had an on & off relationship, but by time she finished she was in front of you and everyone stared "Will you go on a date with me?" She asked which caused you to turn into a blushing mess but you agreed.
Finn:
He had just won a football game and he asked Coach Beiste if he could say something and he looked at you "Okay, so I promised myself I would do this if we won so here we go... Tami, I've had a crush on you for a while now and wanted to know if you would go to breadsticks with me?" Finn asked and you agreed with a smile.
Quinn:
You were at her place practising a duet for glee club when she went to the bathroom and soon she called you in before she pointed to a fogged up mirror "Can you read what that says?" she asked you "Will you go on a date with me?" I asked in reply so she smiled "Yes I will" She said before handing you a bouquet of flowers, it was cheesy so now you tease her about it all the time.
Puck:
It was your birthday and since you had never celebrated it before, you weren't expecting anything but as soon as you entered the choir room you were forced on a chair and Puck stood in front of you "Happy birthday, I was hoping I could take you out to dinner to celebrate?? If my looks haven't already convinced you then let the awesome voice of Puckasaurus convince you" Puck told you so you giggled and he sang Just The Way You Are, obviously you agreed and lets just say, you will never forget that day.
Santana:
She was actually pretty nervous, you were both still in the closet at the time, her being a closeted bisexual and you being a closeted pansexual so she didn't want anyone to find out which is why she had originally planned to ask you out at her place but changed her plans when Finn outed both of you because he was mad at Santana and you just happened to be there. She changed her plan to ask you out after the glee off between The New Directions and The Troubletones. You had just finished your song when Santana got mad at Finn and slapped him because he whispered to Rachel about Santana's crush on you and since you had heard it, you looked at Santana "Y-you have a crush on me?" You had asked softly and she sighed "I was going to ask you out at my place since we were both closeted but then Finn outed both of us so I was going to ask you out after we won this glee off but I guess that's out now as well" Santana had told you so you smiled softly and hugged her "I'd love to go out with you" You whispered so she smiled happily and hugged you back.
Blaine:
You two went on dates often but it was never official so one day he just asked if you wanted to officially date him and you agreed.
Brittany:
She tried baking a lemon drizzle cake since that was your favourite flavour and on top she wrote 'will you go out with me' out of the icing before taking it to school and handing it to you and you saw it before agreeing and she quickly apologised "There are egg shells and I think its under cooked because I can't read recipes" Brittany said apologetically causing you to giggle "Maybe I-I can teach you?" You asked her so she nodded excitedly
Kurt:
He was REALLY nervous so he wrote you a poem, he knew you were a hopeless romantic who found poems and letters etc cute in comparison to text messages so he wanted to make it perfect for you so he wrote
'Roses are red,
Violets are blue,
Will you go out with me?
Because I think I love you'
After he wrote it, he put his name on it before putting it in your locker and heading to glee and when you walked in, you looked at him before nodding with a smile so he mentally punched the air.
Tina:
She sang to you, she never got solo's in glee so she was very nervous but regardless she sang 'Be My Baby' by the Ronettes since she knows how much you love old songs from the 50's/60's and once she finished she was in front of you and you were confused at first until she asked you to go on a date with her so you agreed.
Mike:
He asked you to help him with his audition for the Joffrey Ballet school so you helped him with the dancing but he incorporated a lot more lifts and moves that required you to be close than he usually did so you were already confused and suspicious however you were set to help him so you pushed your confusion to the back of your mind and after his audition, he pulled you to the wings and asked you to go on a date with him and you agreed.
Mercedes:
She had been trying to ask you out for months but she did it in ways that were 'subtle' so you didn't realise, she gave you flowers, sang songs to you and wrote love letters but you didn't even realise until she pulled you out of class and asked you out and you agreed, curiously asking why she didn't ask before.
Sam:
You were helping him take care of his siblings when he decided to sing to them to help them fall asleep and he sang Perfect by Ed Sheeran and once his siblings were asleep he took your hands "Will you go on a date with me?? We can't really do much since I can't afford it but it will still be great!" Sam offered so you smiled at him "I'd love too, why don't we just go on a picnic?" You asked him and he agreed smiling happily.
Sugar:
It was valentines day and you were looking at all the notes in your locker that were asking you to be different kids valentines date and you sighed trying to think of ways to decline without hurting anyone's feelings and then you went into glee club and saw Sugar being serenaded by Artie and Rory but she ignored them before she spotted you and walked over "Will you be my date to breadsticks tonight?" She asked so you blushed and nodded with a smile so she sat beside you and smiled brightly.
Rory:
Him and Artie were fighting for your affection and he sang about being deported so you ran over and hugged him "Will you go on a date with me before I go?" He asked so you nodded.
Lauren:
You were watching one of her wresting matches and she won and once she was declared winner she smiled then made eye contact with you before grabbing a sign which said 'Will you go on a date with me Tami?' and you smiled brightly before nodding so she cheered.
Sebastian:
You were used to meeting up at Lima Bean since you were friends but you always sat in a dark corner because you couldn't let anyone know when he asked to make it official "We've been getting coffee together for months... do you think we could call it a date from now on? I kinda like you" Sebastian told you so you blushed and nodded with a smile.
Marley:
She was really nervous about it and asked Unique how to ask you out and eventually decided to ask you in glee club and she sung 'I'm Yours' by Jason Mraz and she finished in front of you before she grabbed your hand and asked you out so you looked at her before nodding and smiling whilst she hugged you.
Jake:
He was completely smitten for you and wanted to ask you out but your abusive ex had recently been arrested so he wanted to wait but when he saw how depressed and dare I say it.. broken you were, he decided to confess to you and he sang 'Let Me Love You' By Ne Yo and once he finished, you broke down and he asked you out whilst hugging you so you agreed.
Kitty:
She wasn't sure how to ask you but soon decided to get you a stuffed bear since she knows you love soft things and so she went to build-a-bear where she saw a stuffed bunny and she got it and named it and got it a red outfit with hearts over it then the next day she handed it to you and asked you out and you agreed.
Ryder:
You were Sandy in the school's production and he was Danny Zuko, you had already been really good friends but you had gained weight and didn't fit into your costume properly and resorted to puking your guts out and Ryder walked in and stopped you before lifting your chin up "Don't make yourself sick, you are gorgeous and I don't want to kiss a girl with puke on her breath during... or after the performance" He told you so you blushed and then after the majority of the production was over, you changed into the cat suit and looked in the mirror nervously before Ryder spotted you "You look gorgeous" He told you "You don't think I'm too fat? I feel like I'm going to shake out of the seams in the shake shack" You rambled "Don't say that, you're gorgeous" Ryder told you "But... will you go on a date with me afterwards?" He asked you so you looked up at him before nodding.
Unique:
She was planning on asking you to the Sadie Hawkins dance because she knew you were too shy too ask anyone and so she sang 'I will always love you' by Whitney Houstin and asked you so you agreed blushing madly.
Mason:
You were doing a duet in glee club of Will You Love Me Tomorrow/Head Over Feet by The Shirelles (Carole King's version)/Alanis Morissette and once you finished he asked you out and you agreed and hugged him despite Madison disapproving.
Madison:
You were at the invitationals and she asked Rachel if she could ask you out if the New Directions won and she agreed and you guy's ended up winning so she grabbed your hands and asked you out in front of the giant crowd and you agreed.
Jane:
You had both been working on a duet to sing in front of the glee club and since Santana proposed to Brittany a couple of weeks prior she thought it was the best place to ask you out so she asked you to do the duet you had been preparing which was a duet version of K.D. Lang, 'Constant Craving' and once you finished she asked you out and you nodded despite the evident shock on your face.
Roderick:
You had been helping him keep track of his diet and have been supporting him through Spencer's harsh exercise regime and he just asked you one day after his PE class.
Spencer:
He asked you after a winning game, he got the football team to haul him onto the bleachers and he walked to you and asked you out so you agreed.
