Relationships

Should I initiate the conversation twice in a row?

So, there is this really cute guy that goes to my school. He is a student athlete (football (/ transfer student. He's from the north and my school is located in the south (USA) so he has a totally different mindset than most people at my school. He's VERY attractive and all of the girls at my school want him badly!! I've had a crush on this guy for a semester and can't seem to understand him. At my school, its easy to say im very popular, attractive, and morally stable, i hold a prestigious position where i have to speak to everyone on campus. (its a small school). Im the type of girl who is authentic and would rather have a great bond with a guy than have a great looking guy. So, when i first met my crush i really didn't pay him ANY mind. He even had to remind me of his name twice. In the beginning of the semester i would eat with him and some of his football friends out of convenience at first but they became really good friends later on. Before he was my crush it was so easy to talk to him, but one day i realized he started to look at me in a different way. I feed off of people's energy so it was obvious when his changed. I started crushing once I began to catch him staring at me, and so I started shying away (talking less at the table) so when we ate together, it would be awkward for us. Eventually he stopped eating with us. He would eat with other people and then stopped eating all together. I was frustrated all semester bc he never tried to talk to me or ask for my phone number but i would ALWAYS catch him staring at me. So its the break now, and i DM him on ig. I asked him a small question and we started a conversation. Now the conversation kinda died out bc the last this we said to one another was "Merry Christmas" and he told me first. Why didn't he try to continue the conversation after Merry Christmas? Should i send him a Happy new year?
Should I initiate the conversation twice in a row?
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