22 “Hip” Flasks for Happy Hour

1. Talking About Money Can Expose Hidden Feelings

It's impossible to know how someone feels every second of the day, but we probably all think we have a good understanding of the people we're close to. But people are capable of hiding how they feel about something or burying their discomfort until certain situations 'expose' them. Why does it seem like money has a way of doing this?

Both Irwin and Dunlap agree that "money is taboo," leading people to avoid conversations about it. "Data tells us that we are more likely to talk about any other taboo topic—sex, politics, religion, even death—before we’ll talk about money," says Dunlap. West agrees and says, "Money is like that one friend who’s incredibly helpful but totally untrustworthy—everyone likes what they bring to the table, but no one wants to talk about them directly." Did you think of someone specific? It's okay because I did too!

The problem is that money can make "hidden insecurities come out, old sibling rivalries rear their heads," and more, according to West. "Even something like 'who paid for what' can suddenly become a life-or death conversation," she says. It's strange because Irwin says a Wells Fargo study shows that "many Americans across all ages are worried about money," proving we're all thinking about it, despite our avoidance issues.

2. And Money Can Also Create Unease In Conversations

"When we don’t have open conversations about money, we’re left to navigate it on our own, which can keep us feeling underpaid, overworked, or unsure about our financial situation," Dunlap points out. She feels "discussing money requires a huge amount of vulnerability" which "isn't easy for everyone." You may have seen how other topics are swept under the rug by family members or friends based on reasons they're not ready to talk about.

Though Irwin believes saying something like saying, "'Here's what's keeping me up at night' or 'here's what my goals are' could strengthen connections," Dunlap knows that "shame, comparison, or fear of judgement" can cause people to remain tight-lipped about their finances.

If you've experienced a weird moment because of money or had to be the unfortunate witness of an awkward conversation, my apologies. It's not fun no matter who's involved because, unfortunately, "money carries layers of emotions, like pride and insecurity, that turn simple conversations into potential minefields," says West.

Dunlap says there's a silver lining if people are willing to be open, however. "The key is respecting each person’s comfort level, and encouraging openness if they're willing to meet you there. It’s not going to be perfect at first, but by starting to share more about your own financial experiences, you can start to break the cycle of shame and fear around money. You might be surprised at how quickly others are willing to open up too."

3. Making Assumptions About Other’s Money Status And Financial Situation Can Lead To Disrespecting Boundaries

No one's saying you should never lend friends money, but being mindful about the decision is worth noting. West feels "it's complicated" while Dunlap believes the issue "can be tricky." There's a chance a low-key loan becomes an expectation that you should dish out money every time someone needs help, even if you're trying to maintain your own bills. "Lending money to a friend is like sharing your Netflix password—simple in theory, but one wrong move, and things get weird," West forewarns.

Dunlap also says, "When you lend money to someone close to you, there's always the chance that you won’t get it back. You want to be mentally prepared for that! Otherwise, it can strain your finances and your relationship. The emotional toll can be just as heavy, as unpaid loans can lead to resentment or awkwardness." It's not unusual to hear about certain friends being unreliable in more ways than one after you've let them borrow something. Unfortunately, Irwin indicates this happens because some people "don't expect to give something back that they've borrowed."

Because of this, Dunlap thinks "it's best to avoid loans if possible." Should you decide to move forward with helping out a friend who's in a bind, make sure you're both in agreement about repayment and what to expect moving forward. West says "having clear terms" or "gifting a small amount if you can afford it" is like "buying their friendship insurance." The latter is something Dunlap agrees with because it "helps prevent resentment if they can't pay you back as planned." Plus, she feels it also "keeps the loan within an amount you're okay with potentially losing."

4. Lending Money Is A Slippery Slope That Can Lead To Distrust And Resentment

It's amazing how money can lead to a friendship breakup if boundaries aren't created or respected. "Money is a sneaky little devil who can push everyone’s buttons. It can cause resentment if one person feels taken advantage of or someone’s 'casual loan' becomes an epic saga of unpaid IOUs," West says. Not only that, but Dunlap knows "money can strain relationships between friends and family by highlighting differences in how we value it, expect to use it, or feel about sharing it."

Friends and family members shouldn't take each other's kindness for granted, but human nature is fickle at times. That's not an indicator that someone you love is a "bad" person, but they may feel like you owe them your time and money. However, Irwin says this isn't "de facto that that person is entitled." Still, Dunlap is more than aware how this can play out. "For example, it can lead to resentment if one person is always the one picking up the tab, while another might feel uncomfortable or indebted because they’ve been helped financially," she says.

On the other hand, it can show up a little differently in families. She adds, "Issues like unequal inheritance or constant requests for financial help can lead to deep emotional tension. Money can also become a tool for power imbalances, where one person feels in control and the other feels dependent, and that can mess with trust and respect."

When certain negative patterns show up in relationships, it can make people decide to take a step back from being available. "And once distrust settles in, it’s hard to shake; nobody wants to be 'that friend' who’s forever dodging a Venmo request or getting side-eye from relatives at every family BBQ," West points out. How many times have you built up a wall with the people you love because of repeated unreliability or the expectation that you're supposed to help them whenever they ask? If you didn't hesitate to think of a moment, you're living proof that distrust can affect even the closest relationships.

Dunlap says, "When money becomes a main factor in a relationship, it can overshadow the connection, making it difficult to maintain genuine trust and understanding. You can avoid this by having open conversations with friends and family about your financial situation. Clear communication can help keep the focus on the relationship, not the money."

5. You Can Worry You're Not A Good Friend Or Family Member For Setting Money Boundaries

Worrying about how other people feel can keep us from setting boundaries. There's a difference between being an empath and a people pleaser, but it's easy to blur the lines. You can absolutely empathize with someone's hardship while knowing you're not in the position to lend the amount they may be looking for. I'm a huge fan of saying that two things can be true at once — because they can.

Irwin says you need to "address the conversation head on" if a friend does ask you for a loan. Your response may depend on if their ask was "emotionally-charged or "in an uncomfortable environment," but Irwin doesn't recommend ignoring it. If you're not in the space to respond, here's what she suggests saying in a "timely" fashion:

1. "Hey, I need time to think about this. Let me get back to you."
2. "We can help you, but here are our boundaries."
3. "We see and understand you, but we're unable to help because we're trying to pay off debt or save for _______."

Yes, Financial Boundaries Are Essential

Don't think you need to create financial boundaries for yourself and your friends? Think again. West says, "Establishing some ground rules is a lifesaver—think of it adding airbags to the friendship. Setting boundaries early on, like when you’re still in the happy, non-monetary part of the relationship, can protect both sides if things get sticky."

Here's how she advises you proceed with creating boundaries:

1. Keep it light and be honest; you’re not making a prenuptial agreement here, just letting them know you’d like to avoid “financial fireworks” later.
2. Say, “I’m your friend, not your ATM.” It’s funny but helps set the tone that your wallet isn’t a free-for-all.
3. Set a gift cap, such as, "I'm happy to chip in for brunch or a birthday, but let’s not get into home-loan territory.”
4. If you do lend, draw up a repayment plan. Think of it as adulting with a side of accountability to avoid “accidentally” becoming their financial fairy godmother.
5. Limit talk of big financial choices unless you’re genuinely invested together. After all, nobody needs to know how much their friend spends on avocado toast or scented candles, let alone home renos.
6. A little humor and some boundaries go a long way. You’ll save yourself a lot of awkwardness and keep the friendships intact, one “non-loaned” dollar at a time!

Tori says, "It's so important to have transparent conversations about money, set clear boundaries, and ensure that relationships are prioritized in any money exchange." Here are a few things you can try:

1. Communicate about your budget with a “gratitude sandwich.” Say you’re invited to an outing—a dinner, or a sports game—that isn’t within your budget right now. You can respond with the “gratitude sandwich.” The “pieces of bread” are positive, and the “meat” is the money thing you’re scared to say. Thank that person for the invite, let them know it’s not within budget right now, and then offer a cheaper alternative, reassuring them that you’d really love to see them. Offering an alternative reminds that person that declining their invitation isn’t about them, and you still care about them. In doing so, you prioritize your budget AND your relationship in the process.When in doubt, remember that no is a complete sentence. You don’t need to overcomplicate things, and sometimes a simple “no” is all you need.
2. Set expectations early. When planning trips with friends, discuss the budget and how costs will be split upfront. Having these conversations ensures that everyone is on the same page and helps avoid any misunderstandings. It creates a supportive, stress-free environment where everyone can enjoy the experience together without any added worries!

The Final Verdict:

Once you've weighed your options and considered what you need, you can decide to loan your friend money. However, Irwin wants you to consider being formal about it. "You can absolutely draft a promissory note or loan agreement so that your friend knows how serious you are about your boundaries. If you want, you can also put an interest rate on it," she says.

It's not to hurt your friend's feelings, but it is a boundary you can put in place so they think to themselves, "This is truly a loan because I'm borrowing money with the intent to pay it back," Irwin says. It could change the dynamics of your friendship, but it's more about being "purposeful about the language being used" so you and your friend can both move in the "right direction," according to Irwin.

If the idea of creating a 'loan agreement' sounds icky to you, Dunlap wants you to seriously consider it as "an extra bit of protection." She says all you need to do, again, is "try setting up a simple contract to outline repayment terms" because it "can help both of you stay on the same page and avoid misunderstandings down the road."

Her ultimate piece of advice? "Only lend what you're comfortable giving and potentially losing, and keep open communication to maintain trust and respect in the relationship."