Should you try again if he already said no?

Yes, you can but you have to wait a week minimum.

If you give him another invitation too early, you will sound pushy or needy which is a massive turn off!

So when the opportunity rises again, say something like:

“Next week end, I am going on this road trip with a friend to the coast. We take off on Saturday noon and we will be back in the evening. We need someone who can read maps! You can read maps?”

Cool aye?

Here is another one.

“The Rangers are playing and I have two tickets for the game. You already rejected me miserably once the other day, so I am certainly not going to ask you again…”
(Smile – Look in her eyes)

“Maybe I should try with your best friend, Dan… It looks like he’s quite into me…”

“I give you 5 seconds to make a decision…”

Play, with this!

Make sure he understands you are teasing him.

Let him see that if he does not say “Yes” – You already have other options lined up.