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Don't be afraid to initiate a conversation in my opinion even if it is about something little (e. g. Hey, I enjoyed seeing you ____, maybe do it again sometime?) or something where it asks for a response, or a compliment as I believe that it shows the guy that you are thinking of him. I also believe that subtle hints about another date etc and compliments or something that shows him that you went out of the way just to type a text (even if it's a little one) shows that you like him (friend/boyfriend) and are interested in him but the wording etc shows in what way you want to be involved with him (relationship or just friends). Texting him first also may result in a reply that may give hints into what he wants from the relationship or maybe he is just nervous and this creates a way which he can text you? Hope this helps and makes sense. I also hope that everything goes to plan fro you!