Clearly, the right time is different for everyone. But Darr says to wait until I've established that "yes, this is somebody that I feel like I trust" or "this is somebody that I see a future with."
"Then I think it's safe to start to get into the conversations," Darr adds.
It doesn't have to be a tense interrogation. As an example, she says, maybe I mention to Bachelor No. 2 that it's tax season. I volunteer some information, saying I've already started the process of gathering my documents, and by the way, he's started his return, too, right?
"As you're dipping your toe into it, and you get a sense of, OK, we're on the same page, then I think you can really start to get into more serious conversations," Darr says.
I'd be remiss if I didn't mention romance scams here. It's becoming increasingly common for fraudsters to make fake dating profiles and/or social media pages in order to start conversations with strangers like me. We build a relationship, and then eventually they ask for money, often claiming it's for medical expenses, a plane ticket or to help them out of a tight spot.
According to the Federal Trade Commission, Americans reported losing $1.3 billion to romance scams in 2023.
The FTC's rule is to never send money (or gifts, for that matter) to someone I haven't met in person. Similarly, Darr says I should make sure I trust my partner before I start sharing my financial details with them.
I should also be careful not to jump to conclusions. If Bachelor No. 3 tells me he has a low credit score or a big student loan balance, it doesn't necessarily mean he's bad with money.
"It's all contingent on, you know, a series of priorities that person [has]," Darr says.
Fair warning: Guntrip says these conversations can be tough, honest and vulnerable. The willingness to engage can be a good sign, though, and the start of a journey where we learn how to improve our finances together.
"I think the red flag would be if you think you're at a stage in a [relationship] where you should be having those conversations, and that person is unwilling to have that level of commitment," she adds.
