Most Helpful Guy
Whether your talking to a guy or a girl, conversation will often go nowhere if one person isn't trying. That said, the easiest way to get a conversation flowing is ask them something about themselves. Especially in text, if you make a statement without giving them an opening, conversation gets kinda hard. If you get them talking about themselves, it's much easier. Instead of "oh today I went and did ___", try adding a question of them at the end.
Assuming your reasonably familiar with each other, e. g. you've known each other more than a couple months, try sending them a funny picture of something you both like. Ask them advice on something, even if you don't need it. If you recently had some kind of interaction with someone they know/sports team/family, open with that ("oh hey I ran into ___, they're your friend aren't they?""howd you get to meet them anyway?").
Key thing is ask them questions and be ok with NOT talking about yourself for enough time that conversation flows.2THIS IS NOT RELEVANT ANYMORE