You should text him first if, you're reaching out to him to genuinely connect and communicate with him. If for any reason you're texting him based on worry, fear or anxiety. Such as, trying to “keep his interest” or manipulating him to do something for you. Or to fill some kind of void in your life.

Should I just text him how I feel?

There's nothing wrong with telling someone how you feel over text and expressing that you see the connection developing into something more, like an exclusive relationship, Palmer says. If the person you're feeling feels the same way, they'll text you back and say so.

How long should I wait to text him?

You may be worried that you're being held down by the arbitrary "three-day rule," but fortunately, it may turn out you're doing more worrying than necessary. According to experts, the best rule of thumb is that you should text someone within 24 hours after a first date.