As you navigate working life and budgeting the salary that comes with it (Adulting? Who, me?), you’ll likely encounter some awkward situations around money. Handling these moments can challenge your relationships, your patience, your ego — and, of course, your finances.  
Here's what the experts recommend for dealing with some common money situations 20-somethings experience.  

The Situation: You have to ask your roommate for their rent check ... again. 

Whether your post-college roommate is a friend or someone you found on Craigslist, asking this person for money (especially habitually) is not only awkward, it's also frustrating. "Familiarity often leads to shortcuts in considerate behavior and communication, especially in a roommate situation," says etiquette expert Lisa Grotts.  
Instead of handling the finances yourself, request that you both send your respective checks to your building’s management company every month so you're not waiting to get paid, she suggests. You can also see if they’ll take electronic payments from your individual accounts to make it even easier. (The same goes for shared utility bills.) 
If that's not an option, therapist Raffi Bilek, LCSW-C, director of the Baltimore Therapy Center, suggests using this script: "Hey [Roommate], I know you have been having trouble paying the rent checks on time lately. I'm trying to be understanding about this, but I really do need the rent check to be on time. If you are unable to make that happen, I will have to [find another renter, add a late fee, etc.]"  
Even if you're not the assertive type, being straightforward — instead of stewing silently and letting resentment build — is the key to preserving the relationship, he says. Focus on the fact that it's just about money, and not personal, to ease any tension.  

The Situation: You're at a group dinner and the place only takes cash — but you don't have any. 

As soon as you notice the policy, don't sit there and sweat: Tell your closest friend there that you didn't know you needed to have cash, suggests relationship expert Jackie Viramontez. Then, offer to walk to a nearby ATM before you sit down or after you finish your meal. 
"This approach gives your friend the opportunity to be generous by offering Venmo or another payback option instead," she says. "If you Venmo them, add a few bucks as a thank you." 

The Situation: You're taking work clients out for cocktails and your card gets declined. 

Well, that's embarrassing. Bilek suggests brushing it off by saying, "Sorry about that. Must be some kind of fraud protection. Let me grab another card and we'll get that taken care of." 
But if you don't have another card and no cash, discreetly try to resolve the situation, he says, by calling a friend or colleague to come by and spot you — perhaps order another round to pass the time once they've confirmed that they can help you out.  
If you absolutely have to ask the client to pick up the tab, remain calm, use a sense of humor and then move on, Bilek says. Offer to Venmo the amount or take the client out for a nice dinner another time to make up for the mishap.  

The Situation: You're on a date and the check has been sitting on the table, untouched, for 20 minutes.  

Traditional etiquette dictates that whoever does the asking pays the tab on a date, Grotts says. However, if you and your date planned the outing together by collaborating on the details (time, location and so on), the rules get a bit blurry.  
Plus, these days, when people may meet up more informally, the so-called rules regarding who pays can be even more confusing. So, if the other person suggests splitting, don't necessarily judge them as cheap or ill-mannered — they might be trying to respect you as an equal, Viramontez says. Or, if your date is making no attempt at grabbing the bill, simply grab it yourself, pay it and playfully tell them that they can get the next one. 

The Situation: You're planning a group vacation with your pals and the shared costs are out of your budget. 

Figuring out trip logistics with friends can be tough enough, but when you're working with different budgets (and expectations), things can get awkward. The best thing to do, Grotts says, is to be honest and upfront from the start. Know how much you can spend before booking the trip, and let your friends know during the planning stages. "If you take the guessing game out of the equation, there is no stress and all parties win," she says. 
Perhaps your group can opt for more affordable fixed costs like lodging (as in, booking a shared Airbnb that's in-budget for everyone) and then individuals can decide to spring for extras — like shopping or pricey dinner orders — based on how much they each want to spend. Asking your group to buy some collective groceries and eat a few meals in can also help save cash without compromising fun.