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You pick up the bill for dinner, pay for the taxi home or grab a friend's coffee with the promise they'll pay you back later, but days go by and the money never arrives.

At what point do you ask them for it again and how small is too small to chase?

For some, $5 (£3.70) is worth a reminder, while for others, asking a friend to repay anything under $20 (£15) feels more awkward than simply taking the hit.

Henry Payne says he's "sent a request for $8.50, but I wouldn't go lower than $8".

The 21-year-old New Yorker adds that he will chase someone once but "two requests is insane".

"I would rather swallow the $8.50 than send another request."

He does admit that he's sometimes the person on the other side of the transaction and can be forgetful himself.

"For everyone that I haven't sent back money to, I just forgot, feel free to double request me."

Kaz Jahanbini, 19, says needing to ask to be paid back in the first place can be frustrating.

"If someone bought me something, I'm immediately paying them back. So then I'm thinking for them, what's the delay?"

His rule for navigating friendship and finances is to "keep your wallet close but your friends closer".

His friend Nouria agrees and says as a student "every extra dollar counts" but she would usually only ask for money back from a friend if it was more than $10.

A recent study, external found that 76% of Gen Z who have fronted money for a group expense, like a trip or event, say they were not fully repaid, and 55% say it created tension or negatively affected a relationship.

For British student Betsie Brooke-Taylor, 19, the threshold to ask for money back is a fiver as she says "every little helps".

She sees a cultural difference between the UK and US and even though "we are all broke, I think Americans are a bit more generous".

Betsie also thinks technology makes settling small debts easier in the US, where payment apps such as Venmo are widely used.

Venmo lets users send and request money through an app which includes the function of sending a reminder if someone hasn't paid you. In the US, more than 95 million people have a Venmo account, external.

"In the UK you have to ask for the account number and sort code, and not everyone has that on hand," she says.

For 19-year-old Annika Violet, the amount she would ask back from a friend depends on whether she's consistently paying for them.

"I prefer to do something where I get them this time and they get me next time but if I'm consistently paying and you're not, then I will request the $5."

Unlike many, Annika doesn't find money conversations uncomfortable.

"I am so confrontational, I do not find it awkward. If you're my friend, you would pay me back."

Annika's friend Hanako Stepper says she finds it awkward asking for money but wishes she didn't.

"I've never chased anyone - I'm just sad if I don't get paid back."

Annika's advice to those who do struggle to ask is to "be brave and bold".

"If they are going to give you flak about it, maybe it's a sign they are not a good friend."

How do you ask for money back without making it awkward?

Money expert Laura Pomfret says many people feel embarrassed about asking to be paid back, and Britons in particular can find it awkward.

"We're often very British about asking for money back," she says, suggesting people may be worried about being judged as a "cheapskate".

Her top tips for asking friends to pay up are:

She adds that you shouldn't convince yourself that a debt is too small to justify asking for it as "if you want the money paid back then the amount shouldn't matter".

And if the same friend repeatedly fails to pay, Pomfret suggests remembering it the next time you're about to pay for them and think twice.

Several people the BBC spoke to said the amount itself mattered less when somebody repeatedly failed to pay.

New York student Ella Feuille, 21, says $15 is roughly the point at which she would consider requesting money.

If a significant amount was owed, Ella says she would ask around three times before giving up but wouldn't necessarily forget about it.

"I have friends who I know now it has to go on their card because they're not going to pay me back."

Her friend Katrina Dimingot agrees and says she much prefers a method where "we don't pay each other back, we just take it in turns to get things for each other".