My friend's boyfriend seemed perfect until he started asking her for money. We think he could be a con artist — how do I help her?

The offers and details on this page may have updated or changed since the time of publication. See our article on Business Insider for current information.LEREXIS/Getty ImagesFor Love & Money is a column from Business Insider answering your relationship and money questions.This week, a reader worries about the financial motives and situation of the man her friend is dating.Our columnist suggests moving slowly and asking for honest communication.Have a question for our columnist? Write to For Love & Money using this Google form.Dear For Love & Money,A friend of mine has been seeing a guy for about eight months. He's funny, charming, and sweet. He surprises her with flowers, pays for dinners, and talks about their future together.The problem is that things are no longer adding up. His card was declined when they tried to book a weekend getaway; he said the bank must have messed up. Then, she noticed a few $250 Venmo payments on his phone to someone with a female-sounding name. When my friend asked him about it, he said this woman was some kind of accountant. I work in finance, so I know that Venmoing your financial advisor is completely unethical, and I doubt that's what's really happening.Now this guy is asking my friend to cover next month's rent until he gets his Christmas bonus. She likes him a lot, but she's starting to wonder if he's a con artist or just bad with money. How can she tell the difference?Sincerely,Wise to be Worried For Love & Money answers your relationship and money questions. Looking for advice on how your savings, debt, or another financial challenge is affecting your relationships? Submit your question in this Google form. Dear Wise,Like your sign-off suggests, your friend is wise to be worried. Your letter reads like a list of red flags. Even the positive parts are suspicious against the backdrop of the rest. Is he even sweet and charming, or has he just been love bombing her? They're only eight months into their relationship, so it's hard to know yet. And that's the rub.When you really like someone, like your friend does, walking away over a question mark is a pretty unreasonable expectation. Whether that skepticism is coming from you as a friend who cares about her, or from deep down within herself, she will always weigh it against, "But what if I'm wrong about him?"But the other side of that question, of course, is: "But what if I'm not?" And the answer to that can range from a disappointing breakup to utter tragedy — in this case, potentially financial.Before your friend even considers lending her boyfriend rent money, your friend should insist on a transparent conversation with him about his financial situation. Combining or exchanging finances with a significant other is always a huge step, and should begin with an open discussion of preferences and boundaries in any relationship.The questionable behavior of your friend's boyfriend only adds more weight to the conversation they must have. She shouldn't shy away from asking him the awkward questions — about the time his card was declined, the mystery Venmo payments, and how he plans to handle rent for the rest of the year before he supposedly receives his Christmas bonus.But she should also go beyond that, like discussing why he's in a position where he needs her to lend him money and how they plan to handle finances moving forward in their relationship.Encourage her to be firm in her pursuit of answers. In the best-case scenario, he might open up about what's really going on, and she'll learn he's not great with money, or maybe he's actually just facing an understandable setback. In either case, she will have to decide whether she trusts his explanation and whether his financial troubles are something she feels prepared to take on.However, he might brush her off or beg his way out of the conversation. If he does do either of those things, I'm afraid that's her answer. He also may slide out of the conversation with an almost-reasonable explanation that still doesn't feel quite right, and she'll have more doubt than before.If this is the case, and she's not ready to end things, you may feel you want to investigate on her behalf. After all, you've already reached out to me to ask about it. This is the part that can get tricky as a friend. It's essential that you proceed with caution, and with her full approval, to ensure she doesn't feel betrayed and blindsided by anything you uncover. Remember that she likes this guy and likely wants him to turn out to be as incredible as he seemed at first.Speaking from my own experience, I know it can be easy to get caught up in the pleasure of other people's drama, especially if the details end up being salacious. For example, if I were you and there were a moment when it started to look like this Venmo woman could be a secret wife, I may find myself hoping she's indeed his secret wife. Not because I'm rooting for my friend's devastation, but because a secret wife is way more exciting, and my friend should recognize that this guy isn't a catch in either case.But also, the mystery Venmo woman may just be someone who sells him collector's edition action figures, and he's too embarrassed to tell your friend he spends that kind of money on toys. Jumping in with dramatic assumptions could hurt your friend — and your friendship. So, lead with this empathetic understanding, even in your function as the clear eyes to your friend's blind hope.The best way to ensure your friend's boyfriend is who he claims to be is to look into his background. Does he have friends and family? Eight months in, your friend should have met many of the people most important to him. If she has, and they all engage with him as the person he presents himself as, that's an excellent sign. You can also look into the woman from Venmo. Are there any financial advisors with that name? Can you find anyone with that name on his social media?Another option your friend has, if she can stand it, is to move very slowly and resist getting caught in a whirlwind of romance and fast-paced entanglement. She can refuse his loan request, but suggest other ways she might support him so he can make rent. This could be a tense line for your friend to walk — showing up for her partner in a way that reflects her feelings for him while also protecting her financial interests.If she can achieve that balance, however, she will have the opportunity to see how interested he is in a relationship that doesn't financially benefit him, and give her more time to become acquainted with how he handles his money.Whatever happens between your friend and the man she is seeing, remember she will always need your support. Whether that's a shoulder to cry on if they end things, a listening ear as she processes her doubts, or a sharp-eyed realist at her back, the important thing is that you aren't going anywhere.Rooting for you,For Love & MoneyLooking for advice on how your savings, debt, or another financial challenge is affecting your relationships? Write to For Love & Money using this Google form.Read the original article on Business Insider

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