It might tell him you are someone who is willing to give first without demanding recompense

On the surface, this is a minor decision. To the cheapskate, the best decision is obvious. If he sees you in that light, a relationship might be seeded by this small investment on your part. It depends on your assessment of his character. In the first case, you are richer in a potentially lucrative business relationship.
_

Apolonia:
I think a guy at my college likes me.
(2 October 2016)

Dolly:
Help on one year with boyfriend plans??
(2 October 2016)

Mamie:
I'm just anxious, I guess, because I've wanted this for awhile.
(2 October 2016)

Mamie:
Our friends all told me to wait and talk to him, but I don't know.
(2 October 2016)

Mamie:
Like, should I wait it out or should I move on?
(2 October 2016)

Mamie:
I'm not sure what I should do, in terms of waiting?
(2 October 2016)

Mamie:
I talked to a mutual friend and the guy apparently told our friend that he's second guessing it because of his track record with girls in the past and that he doesn't want that with me.
(2 October 2016)

Mamie:
But in the last few days, he's been really distant.
(2 October 2016)

Mamie:
I've gotten close with his friends, he's gotten close with mine.
(2 October 2016)

Mamie:
He told people he liked me, he was going to ask me out, we've kissed a few times, and we've hung out plenty of times.
(2 October 2016)