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dating coach for smart, strong, successful women Evan Marc Katz
You suggest we be cool and keep conversations light at the beginning phase of relationships. I’ve got a question: when is the appropriate time to bring up more serious stuff and how to initiate the conversation?

My boyfriend and I are 3 months into our relationship. Both of us are 37 years old and pretty serious about our relationship. I have talked to my friend about my relationship, and she suggested I find out asap what our plans are in terms of financial planning, combining assets, whether or not staying with in laws in future, otherwise I could easily waste another year of my life on the wrong guy. I was a bit worried it could still be too early in our relationship to mention all these things, should I wait patiently for my boyfriend to bring them up later on?

Warm Regards,
Amy

This is an important question, Amy, with a largely dissatisfying answer.

As I wrote in Why He Disappeared, you’re trying to read the last page of the book without reading the book.

I understand why. You’re 37. You don’t have time to waste. You’re not fucking around.

You’re 37. You don’t have time to waste. You’re not fucking around.

But that doesn’t make interrogating your boyfriend a good dating strategy.

If you were to “ask him about his plans in terms of financial planning, combining assets, and staying with the in-laws in the future”, you would, indeed, be addressing some of the most important issues that affect young couples.

You’d also come across as fearful, anxious, and controlling.

I can almost hear the protests from here:

“So, what, I’m not ALLOWED to talk about the very issues that will impact whether we have a future? I’m just supposed to SHUT UP and ACT COOL even though I’ve been burned before and have a very real ticking biological clock?”

Um, sort of. Here’s why:

In my experience, there is an organic way information comes out with two adults: natural, organic conversation, as opposed to “Okay, Tim, what do you think about pre-nups?”

You know how my wife knew I wanted to get married? I talked about wanting to get married.

You know how my wife knew I wanted to have children? I talked about having children.

You know how my wife knew I was fiscally responsible? I talked about saving, credit ratings, buying a house and retirement.

My point is that she never had to sit me down and say, “What are you thinking?” because I revealed it voluntarily. Your boyfriend should, too. That’s what people do as they get to know each other: exchange information. That information either brings us closer to each other or pushes us further away. You needn’t have an “agenda”; you just need to talk like normal 37-year-old adults who are in love and thinking about marriage.

You needn’t have an “agenda”; you just need to talk like normal 37-year-old adults who are in love and thinking about marriage.

And if you have a boyfriend who doesn’t talk and doesn’t reveal what he’s thinking, my first question for you is: why? Why would you be with a man who shares nothing about his feelings, hopes, and aspirations? Why would you settle for a relationship where you don’t know what makes him tick, where you never know he stands, and you’re afraid to ask?

Listen, I don’t know you, Amy, and I certainly don’t know your boyfriend, but every time I’ve heard a question like yours, it’s coming from a place of fear. In your perfect world, you’d hand your first date a questionnaire and he’d answer everything the way you wanted to and you’d live happily ever after. In reality, getting to know each other is a more gradual process that can’t be accelerated or improved with questions about marital finances.

In reality, getting to know each other is a more gradual process that can’t be accelerated or improved with questions about marital finances.

Is it possible you’ll waste your time on a guy who has different values around money? Sure.

I think it’s more possible that your boyfriend will fall more deeply in love with you and be more willing to compromise with you, specifically because you’re not pressuring him to figure out your future after three months together.

I know it ain’t easy, but I think there’s great value to letting people reveal themselves over time instead of demanding that they submit to a panel of serious questions from someone who is afraid of making a mistake.