If you're a serious person, cracking jokes is your highway to hell in the courtship process. You'll always look too try hard and needy.
The secrets to being playful are: (1) Role playing; and (2) Incongruence. But of course, it takes time to learn these two skills. You'll have to start somewhere easier.
Get Into a Funny State
If you're not naturally funny, watch 2 or 3 episodes of Mr. Bean before you go out sarging. Do this for 21 days or around 3 weeks. If Mr. Bean can't make you laugh, choose shows that make you laugh. Everybody has a particular preference for a certain type of comedy. Maybe it's Cheech and Chong that gets your funny bones, or Leslie Nielsen, or Mike Myers. Take your pick and start from there.
Familiarize Yourself with Playful Body Language and Teasing
Go to a park and watch children play. Watch how the little boys tease little girls and then focus your attention on the little boy who makes the little girls giggle a lot. Get your eyes sharp and listen hard. Do this every weekend at least 10 times.
Role Playing, Incongruence and Managing Outcome Dependence
You'll only get to understand role playing after watching little boys and little girls tease each other at the playground. Calibrate though on the roles that you're going to play. Go overboard and you'll look like a nut case. Play it down and you'll have no memorable impact whatsoever.
Personally, I role play myself as the conservative gentleman and the girls I sarge as creeps who want nothing from me but to fuck my cock. Girls who are attracted to you will play along the roles you frame them on while those who are not attracted to you will give you dirty looks.
If it's the second case, act like nothing happened, eject, and sarge the next set. When I sarge, I sarge 3 to 5 sets moving from one set to the next and then going back to the first set for a second round of sarging. In about one hour, I'll have around 3 to 5 rounds of sarges for 3 to 5 sets of girls.
The secret to managing outcome dependence is action; lots of it. If you're sarging so many sets at the same time, action dampens down any form of thinking. You can think later after the sarges and not during the sarges since you're too busy to be even thinking about anything.

_________________
Approach. Open. Escalate. Isolate
Here are my two essential rules on texting that will save you tons of time and money:
general-questions/topic137931.html