9 tricky money conversations and how to ace them, by a top financial advisor

You’ve only had tap water, they’ve been knocking back the champagne, and then they ask you to split the bill. If awkward money moments like this fill you with dread, then you’re not alone - and, the good news for your bank balance is that millennial money guru Bola Sol is here to help.

A certified financial advisor and magazine money columnist, she’s already the author of the best-selling book How To Save It  and also shares her real-talk tips on Instagram (where she has 34k followers).

Now, she’s spilling all of her best secrets in her new book, Your Money Life: How to Afford the Future You Want, which aims to empower us with the concrete skills to become financially healthier, wealthier and happier.

Money is an especially loaded (forgive the pun) subject for women: "Despite strides in gender equality, the gender pay gap remains a stark reality, making financial conversations not just about pennies and pounds, but also power, independence and self-worth," says Sol.

Yet, we’re not just talking about the nitty gritty of pensions, mortgages and investments (although her book does deep dive into these important topics in a way that won’t send you to sleep). "Money is one of the most potent yet taboo topics in any relationship, be it with friends, family, or partners", says Sol. "But the ability to have these conversations with grace and strength is just as crucial as the numbers in your bank account - and having the right phrases at your disposal can make all the difference."

You might assume that this would include an element of grovelling, but no. "As women, we’ve been conditioned to apologise far too often, but there’s no need to apologise for owning your financial narrative. Money is power, and discussing it confidently isn’t rude—it’s necessary. Every conversation about finances is a step towards taking control of your life, your independence, and your future. So, speak up, set boundaries, and never feel the need to say sorry for it."

So, we tasked her with some of the trickiest money conversations - and she has revealed nine powerful phrases to keep in your back pocket, to navigate the choppy waters of money and relationships. As Bola puts it: "Let’s take the awkwardness out of money talk, one conversation at a time."

1. Splitting the bill in a restaurant

Money problem: You’ve chosen budget dishes and you’re not drinking wine, so you don’t want to pay for your friends’ extravagant orders.

"When you're out with friends, the bill lands on the table and it’s an awkward moment: especially if some people ordered the lobster, while others stuck to a salad. To avoid this anxiety of splitting the bill unevenly, suggest from the start that everyone pays for what they’ve had. This sets a fair tone without anyone feeling short-changed or pressured to subsidise someone else’s meal."

What to say: (Before you order) "Shall we all chip in for what we have?"

2. A family member asks to borrow money

Money problem: You’re either unable or unwilling to oblige.

"Money and family can be a tricky combination. If a relative asks for a loan it’s important to set boundaries while still offering support. This phrase allows you to decline the request without closing the door on the conversation, while potentially leading to other ways you can help - such as offering advice or helping them budget."

What to say: "I’m not in a position to lend right now, but let’s talk about how else I might be able to help."

3. Chipping in for a group gift

Money problem: It’s way beyond your budget, you barely know them - or you don’t like them all that much.

"Group gifts are a lovely idea in theory, but when the suggested contribution is more than you’re comfortable with, it can be stressful. Rather than saying nothing and feeling resentful, be honest about your budget. Offering a specific amount you can comfortably contribute shows that you still want to be involved without overextending yourself. It’s all about balancing generosity with your financial wellbeing."

What to say: "I’m on a tighter budget this month, would it be okay if I contribute X amount?"

4. Your partner is over-spending

Money problem: You discover that your partner has spent a significant amount of your joint funds on a frivolous purchase for themselves. How do you express that this behaviour isn’t acceptable?

"Money in a partnership is about trust and respect. When one person overspends without discussion, it can feel like that trust is being broken. It’s not about the purchase itself but the principle of transparency and teamwork. You should never feel afraid to address financial concerns, because an open dialogue is the only way to maintain financial harmony."

What to say: "I understand you were excited about this purchase, but using our joint funds for something we didn’t discuss feels unfair. Let’s talk about how we can manage our money better together moving forward, so we’re both on the same page."

5. Pricey social invites

Money problem: You’re invited to a social event that’s above your price range by a friend who earns more than you, and feel too embarrassed to say no.

"We’ve all been there—invited to an event that’s just a bit too pricey for our liking. Rather than stretching your budget, offer a more low-key alternative. This not only saves you money but also reinforces that your priority is spending quality time together, not just splashing out."

What to say: "That sounds like fun, but I’m watching my spending at the moment. How about a cosy dinner at mine instead?"

6. Asking your family for help

Money problem: You’ve been hit by some unexpected costs, and need to ask your parents for a loan, but feel too awkward.

"Asking to borrow money is never easy, but being direct and clear about your intentions can ease the awkwardness. Make sure you specify why you need the money, how much you’re asking for and exactly when you plan to repay it. This shows that you’ve thought it through and are taking the loan seriously, which can help maintain trust in the relationship."

What to say: "I’m in a bit of a financial pinch, and I wanted to ask if you’d be able to help me out with a loan. I’ll make sure to pay you back by X date."

7. Navigating the dating tab

Money problem: You’re dating someone new, going for dinners and to events - but don’t know how to broach the topic of who’s paying for what.

"When you're on a date, especially in the early stages, the question of who pays can feel like a test of both tradition and equality. To navigate this, ask upfront how your date prefers to handle the bill. This neutral phrasing shows that you’re open to discussion and respect their views, whether they lean towards splitting the cost or taking turns. It also opens up a conversation about finances early on, which can be crucial for setting expectations later down the line."

What to say: "How do you usually like to handle the bill?"

8. Getting out of expensive hen dos

Money problem: You’re invited on a weekend away for a friend’s hen do - and you either don’t have the cash, or simply don’t want to go.

"Hen dos, weddings, and all the associated festivities can quickly add up, and sometimes, they simply don’t fit into your financial plans. If you're faced with a request that’s too much, be upfront. Express your enthusiasm for celebrating but explain that the cost is beyond what you can manage. Suggesting an alternative way to celebrate shows that you value the friendship, even if you can't partake in every event."

Phrase: "I’d love to be there, but it’s a bit out of my budget right now. Could we do something special together another time?"

9. Different spending power in a relationship

Money problem: You are in the early stages of dating someone new and have noticed that your partner spends more than you, and, you suspect earns more than you.

"Money is a big part of any long-term relationship, so it’s vital to discuss your attitudes towards it sooner rather than later. By framing it as a conversation about perspectives rather than specifics, you make it easier for both of you to open up. This can lead to important insights about compatibility and help prevent financial disagreements later down the line."

Phrase: "I think it’s important for us to chat about our views on money—what’s your relationship with it like?"

Bola Sol is the author of Your Money Life, £15.63, out now.