Lol'd at talking about putting the balls into the hole, and come see how stif my shafts are

Dude, this chick seems to go out of her way to hang out with you. Grow some confidence, she's into you (especially when she can handle your DRUNK ass). How many signals do you need? Big spot to her for who pays for the round is a good idea, paying her round when SHE invites you is not

Nice!

Wow...it seems like you could have shipped this weeks ago. I would ensure the beers are plentiful out on the crs.

I would spend the round talking about the cart girl's tits. Or maybe her ass depending on what her best asset is

get some 1-liners from caddyshack ready. oh golly i'm hot today!

When you are driving the cart and the fairway is to your right and you're driving up to your tee shots, make sure you make a HARD right turn into the fairway so that she slides into you, then point at the sign and remind her "90 degree rule".

On par 4 and 5s where the fairway is to your left, make large radius turns to ensure she does not fall out of the cart. If she questions you about the inconsistency just be like "Hey - remember that one time..." then tell some story.

to Caddyshack lines provided she knows them.

Seems like she's into you. Just chill out and have a good time. The gambling thing is a good idea - just make sure whatever you're gambling for is a comfortable amount yet you can still get some good trolling in about the bets. Just let the conversation flow naturally and you'll be fine.

I know from experience, do not pay for her when she invites you.

In fact I would show up early, pay for myself and wait for her at the practice green or driving range to avoid the awkward moment

You are better off bringing some drinks if you want to make a kind gesture

lol dating advice itt

I'm trying to imagine how thin the overlap between "people who go to the internet for conversation topics for a date on a golf course" and "people who can implement dating advice from the internet" is.

I'm picturing two circles that don't touch.

There is no need to be upset

any updates?

when are you playing?

If she is competitive you wont have to say much, and be your self. Smoke a J before to take the edge off.

Played few days ago, it went as expected. Nothing special to report, as usual I shined in the first couple hrs and fizzled later on. Happens to me all the time, great in the beginning but down the road they eventually find me not to be so interesting and very ordinary.

Golf was always fun, as mentioned I didn't want to come off as cheap but also wasn't sure of what the correct play was in regards to the golf tab.

I arrived 20min before the scheduled round and she was drinking coffee in the clubhouse restaurant. I joined her for a bit then dropped off my change of clothes in the locker. BS'd a bit on the practice green and I suggested a little guessing game, loser pays for the round. She is wealthy so obv no probs, the game was to guess the other person's final round score, closest estimate wins. Each had 2 guesses, we write down the numbers and reveal at the end. I guessed her score would be either 96 or 92, she shot a 94. She wrote 85 and 87 for me and I shot 88. So she won that and I paid for the round. It was fun, worked out real well. Great sweat towards the end, as we are both trying to guess what the other wrote down.

Throughout the round, we gambled and had fun. At around the 7 hole, I really struggled with having anything creative or witty stuff to say. Ended up just doing normal dull conversational crap, she hears this stuff everyday so I failed to be different I suppose. I put a lot of pressure on myself to perform and that's totally uneccessary, my friends needle me on that all the time but I can't help it.

We both had fun and that's all that matters, but I really wanted to blow it outta the park and was unable to do so. Her restaurant has some golf party event next week and I am automatically booked in her foursome. Playing with another couple. Will be fine, golf is a ton of fun. Would be better if I learned how to hit my driver! Can fade, can hook but just can't hit it straight.