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

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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?

SilhouetteAww, 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?

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

  1. I wish we had talked more about how much time we would spend with our families. Before we got married it wasn’t a big deal if he spent time with his family every weekend, and I went occasionally. After we got married he assumed that I would go with him every weekend, and I assumed that things would stay the same as before. It is something we have compromised and worked on, but it would have been nice to talk about each of our expectations before the wedding.

  2. Agree 10,000% about getting to know your dude over time… let these questions come up, and come up again, because sometimes people’s first reactions aren’t where they end up. I’ve been with my guy for more than 5.5 years (we’re marrying next month), and it’s been a delightful and educational journey..

    • Totally! I knew pretty early on too…(in fact I didn’t pursue him till I was pretty sure already, but that’s for complicated reasons that are irrelevant to this discussion)…but he’d had his heart broken in a previous very long term relationship in which they had discussed marriage so I knew I had to be patient and wait till he was ready. We’ve been together 7.5 years and just got engaged last month. There’s still things we’re discovering about each other but all the big questions have come up and been hashed out long ago. Not saying you should wait that long, just sharing my experience 🙂

  3. My fiancée and I have both agreed that we actually will never lead into a question with something like “Can I ask you something?” or “This is pretty heavy–is this an okay time?” We both freeze and feel terrified for that split second between the lead-in and the question. When, in fact, talking about these “big issues” is always not at all scary for either of us. If we find ourselves treading emotionally wrought waters, we just calmly ask for a rain check and come back to it later.
    The important thing to know in initially talking about BIG ISSUE is that you don’t have to come to an agreement, compromise or decision. You don’t need to agree, you don’t have to find common ground. Not yet. Just finding out where you each stand and letting that sort of marinade in your minds is key. Then, later, you can revisit.

    • I want to second this. My husband and I started dating at 16. He didn’t want kids, I wanted five. He wanted to go ahead and get married, I wanted to wait until at least 21. He hated organized religion, I couldn’t imagine a family with out passover seders and binai mitzvot. But we were sixteen, so it didn’t really matter.

      Two years later, when we graduated from high school and surprisingly stayed together, we revisited everything. After all, if we were going to actually stay together long term, we needed to know if it could work. He was willing to accept at least one kid and “see from there” and he’d spent enough time at my family gatherings to determine he could be comfortable participating in Jewish family life.

      People change. And people who mesh well tend to shift toward the middle and compromise almost with out realizing it. So feel free to bring up some curiosities (rather than a scary “Can I ask you something” you could segue with something like “So I realized we’ve never talked about how we feel about ____”), but don’t be broken hearted if his answer doesn’t match yours right off the bat.

      • “And people who mesh well tend to shift toward the middle and compromise almost with out realizing it.”

        I totally agree with this. My fiancée and I have done this time and again. The other day I was talking about something, and he just cocked his head to the side and said, “I thought you said before that you didn’t want to do that?” I just sort of stopped and realized that I know I’d always felt that way, but at some point, I’d changed my mind. Without knowing it, without ever thinking consciously about it. It was something he wanted, but I had been against.

        A big part of that, I think, is experiencing life together. Seeing your S.O. in different life situations and getting to know the ins-and-outs of their standpoint can completely alter your way of thinking about what a life with that person would look like. It’s a part of your own personal growth as well as your growth as a couple. Because we’re all always still growing!

        • This has happened to me several times!! I thought I was being wishy-washy, so happy to hear it put in this perspective!!

    • Agreed on this.

      It’s a much smaller deal but the other week my boyfriend suddenly came out with “Can I ask you something? Would it be ok if we met up with someone at *gig*?” (sounding nervous) where normally he’d just say “X is going to meet us there”. (Even if I have no clue who X is.)

      It turned out he wanted to make sure I was comfortable with it because the ‘someone’ was an ex-girlfriend (ended welll a long time ago, both moved on completely) but even so I was completely fine with it, what made the conversation awkward was the big “I am going to ask you something you might not like” entry into the conversation.

      • I know! Even in that split millisecond between intro and question, I’m like “OMG he’s going to ask me if I can make the house payment” or “He’s going to ask me if it’s okay that he invited his parents and the house is a wreck so we’re going to have to clean for a million years!!”
        And, really, it sort of makes the question a little suspect. You’re suddenly irrationally suspicious of why they’re asking, like, why? Is there some REASON I would mind–even though you aren’t actually suspicious of your significant other at all!

        • ahaha- that reminds me of how my dad starts money conversations with “Can I ask you a personal question?”

    • Agreed. My fiance didn’t want any kids when we first started dating. I knew that I wanted one child, and that not getting the opportunity to experience that would be a dealbreaker for me.

      We talked about it. A lot. It was essentially therapy, for both of us. And eventually he came to realize that the reason he didn’t want kids was that his parents were truly terrible parents, and there was no partnership, and there was very little joy in their experience of child rearing because they didn’t create any for themselves.

      Once he realized that he was not his parents, that we had a much more collaborative partnership, and that raising children cam with great joys as well as great burdens, he decided that he definitely wanted to be a father to our child someday. Really it was the fact that he could do wacky science experiments with them and turn them into baby nerds that swayed him. And I sobered to the harsh realities of child rearing instead of my solely rose-colored-glasses view. It’s our differences in personality as a couple that helped us both reach a middle ground on that, and so many other issues.

      • exact same thing with me only roles reversed, I was set on not having any kids (I thought I would be a terrible parent) FH wants kids very much and while I’m still a bit nervous on the idea he brought me around with the promise of making our child a super geeky, super cool kid.

  4. This is a great post! I have been personally polling my married friends with the same question of “What kind of things should we get talking about?”
    And while the honey and I are both OK with having these big conversations, he’ll often just out of nowhere after dinner say, “When do you think we should buy a house”. Short stammer from me, and then I usually ask for a bit of time to think. Then, we sort of work our way into the full blown convo.

  5. My partner and I have been together for about a year and a half and, like you, I know I want to be with him forever. For us, the topic of getting married came up when I first started having visa problems. I’m American living in the UK, he’s English. After those problems sorted themselves out we decided that, while we definitely want to get married someday, right now isn’t the best time, I’ve just started my PhD. I would say, echoing people above, that if you’re sure about him, make sure the time is right to start the discussion, but also to let the conversation come up naturally.

  6. Lol, I thought you were going to suggest taking some hallucinogens beforehand. Definitely a deep conversation mode…but you may not remember it later. And it might not make sense. 😉

  7. I just want to agree wholeheartedly with the point about big topics coming up organically. We’ve had so many talks about how we want to raise our kids (someday) after seeing badly behaved kids at the supermarket!

    I’m not married yet, but my list of things to talk about in some kind of marriage-prep setting is: divorce, general conflict resolution, household management, financial roles (ie, who brings home the bacon), family/holidays, life goals.

  8. I was at that point to when I first started dating my fiance. About 4 months in, it just suddenly clicked, and I was thinking,
    “I’m totally gonna marry this guy.”

    I got excited. REALLY EXCITED. But I had to force myself to calm down so I didn’t jump on topics like babies and houses and OMG MARRIAGE, and proceed to freak him out.

    The topics came with time. We’d just be talking, then all of a sudden we’d get onto talking about housing. A year later, his sister-in-law was pregnant and we started talking about kids.

    It’ll all come organically. I’ve been with my fiance for almost 5.5 years now. We got engaged at 5 and a couple of months.

  9. Though we’ve already talked about it Fiance and I are going through a bunch of the big topics again so we’re both on the same page before the wedding.

    Cheesy as it sounds, we got one of those workbooks for engaged couples (I don’t know the name of ours, but it’s good. I’ll find out when I get home) and will get a bottle of wine and go through a chapter or two.

    • We’re reading 10 Great Dates Before You Say “I Do” by David & Claudia Arp and Curt & Natelle Brown. I live in TX for about 6more days, and he’s in VA. We’re doing each activity over the phone. But, we’ll be driving cross country in my move to VA an stopping at Diners, Dives and Drive Ins restaurants and redoing each date. I’m almost as excited about this journey as he is. =D

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