What Timothy Leary can teach you about having BIG CONVERSATIONS with your potential fiance

By on Jul. 7th
I'm not yet an Offbeat Bride — right now I'm an Offbeat Girlfriend Intending to Propose at Some Point Yet to Be Determined. I've been dating my beau for about six months, and a few weeks ago it just clicked with me that I want to marry him. But we haven't yet had any conversations about married life or other big deal-breaker questions like kids and money.

I know we need to have those conversations before I pull out a ring and pop the question (and yes, I plan to use a ring), but I'm at a loss for how to do so without seeming like I'm going through a laundry list. How can I do this right?



Aww, congratulations on perhaps finding an awesome partner, and double congrats on your plans to propose. SQUEE! Exciting.

So, the only way big conversations are going to feel like you're "going through a laundry list" is if you bringing them up one after the other after the other in a short period of time. Do not rush the process of getting to know your partner. I know it's exciting to feel like OMG THIS IS IT, but take it from me: I knew pretty much within a week of making out with Andreas that I wanted to be with him for the long haul — but we didn't get engaged for six years.

There's an impulse to seal the deal NOW when you feel that rush of OMG THIS IS IT endorphins — but take your time in getting to know your partner, and the Big Deal talking points can arise naturally over the course of months or even a year. Or, heck, if you're crazy slow-pokes like us, even five years — although I'd argue that most of our Big Conversations happened over the course of the first couple years.

When you take your time, you can let these Big Conversations arise organically — ie, you have dinner with a shared friend who's having problems paying their student loans, and then on the drive home you start talking about your own finances and how you both feel about consumer debt, budgeting, and saving.

But sometimes, some things just don't come up naturally in conversation. You have to plan it! In that case, it's a delicate game of set and setting – which is actually a Timothy Leary concept that's usually applied to drug use. But, uh, it's perfectly applicable for Big Conversations too!

Here's the general idea: The set is the mental state a person brings to the experience, like thoughts, mood or expectations. The setting refers to the physical or social environment. In other words, make sure you're both in the right set/mindframe to have a big conversation (is anyone stressed? rushed? irritable? hungry? feeling insecure) AND you're in a good setting (not going to be interrupted, not shouting over loud music, not going to be overheard, etc).

My favorite settings for Big Conversations:

  • Long drives
  • Relaxed brunches (dinner feels too serious!)
  • Walks
  • Cuddle sessions that are NOT foreplay or post-coital

Before launching into a big discussion, test the waters — "Is now an ok time to ask you a big, sorta philosophical question?" Be ok with it if your partner says no sometimes. Remember: there's no rush. If you get a no every time you ask to talk about bigger issues, then you may have a communication issue there that you'll want to address before thinking about getting engaged.

If you're mulling over what topics to discuss, there are entire books dedicated to that subject, so it's a bigger issue than I can get into in a blog post.

But I will toss it out to my currently married readers: what topics do you wish you'd discussed before getting married?