Should I venmo request for a cocktail?

So im currently urban camping in the bay area while a prestigious conference is in town. APEEN or something similar, mind space to current events needs some work. I wake up around 1145 and go to the startbucks for wifi, late morning routine, and expenses. A short brunette catches my eye, we make brief eye contact and the hunt is on. She orders and turns away, I spot a left over bagel on the next table and proceed to be pick up the prize while in transition for the entry. I approach, I smile, she scowls, but Im commited and in deep. "What do you give a girl that has everything... bagel" "I dont know" "cream cheese"


I pull out sandwich baggie of cream cheese out of my pocket and she is awestruck. Left hand is spreading the bagel slices with thumb and pointer. Right hand is knifing and spreading the cheese with surgical precision. She is completely swoon and over the moon. The future life flashes before my eyes and I am filling her bagel with the creamiest of cheeses. We finish the mish mash, peasantries, and exchange contacts. I have no phone so I tell her to meet by the park tomorrow. People watching, lots of bum activities, minimal expenses. We spend the day exploring and getting some fresh air. A urban camping neighbor spots me in the park and waves hi. She asks if I know him and I reply that no. I think hes tweaking on some fenny. She suggests a bar and to grab cocktails. I enthusiastically say yes. This chick. We grab cocktails. I pay. She tells me afterwards that she has a bf, wtf. 

Obviously currently in a constrained fiscal situation. We agreed to hang out in a few days, how should I ask her for money back on the cocktail?

 

So this is what consultants do when they're not on a project

 

Oh, what a wild ride you've been on! Now, about that cocktail money, it's a bit of a tricky situation. You don't want to come off as petty, but I understand that every dollar counts when you're in a tight spot. Here's what I suggest:

  1. Be honest, but light-hearted: You could say something like, "Hey, I had a great time the other day. But I'm in a bit of a tight spot financially at the moment. Do you think you could Venmo me for that cocktail? No worries if not, just thought I'd ask!"

  2. Offer a trade: If asking for money feels too awkward, you could suggest a trade instead. Maybe there's something you can offer in return, like a favor or a skill you have.

  3. Use humor: A little humor can go a long way in diffusing an awkward situation. You could say something like, "Hey, remember that cocktail? I think it's come back to haunt my bank account. Any chance you could help me out?"

Remember, the key is to be respectful and understanding. She might say no, and that's okay. It's a learning experience for next time. Good luck!

Sources: Recommended Drinks?, Fired from PE firm for getting too drunk at company outing, HELP! My boss won't give me money!!! what to do???

I'm an AI bot trained on the most helpful WSO content across 17+ years.
 

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