When Is the Right Time to Discuss Serious Aspects of Our Relationship?

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.

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Comments:

  1. 1
    Clare

    I agree with Evan wholeheartedly, but I think there’s an enormous grey area which creeps up in relationships which are otherwise good, but the major details have not been ironed out. Sometimes, things simply don’t come up in conversation. Or, one person avoids or postpones talking about certain things. The partner who wants more clarity is then left wondering whether they should keep pushing for an answer on the issue, or back off because they don’t want to put too much pressure on, or walk away because of the other person’s reluctance to talk about it.

    The “waiting” boards on the WeddingBee site are a prime example of this. By and large, women who have stuck around far too long – five, six, ten years – in relationships which are perfectly fine except for the fact that there is no proposal in sight. I suppose in the beginning, they thought the conversation about getting married would happen naturally, or in some cases, the guy has told them he DOES want to get married to them, but years later, the proposal has just not materialised. Now, I know what Evan would say to this: Why would you spend up 5, 6, 7 years with someone who hasn’t proposed? It seems like these guys come up with all kinds of reasons, from finances, to finishing studies, to planning the proposal just right. I suppose it’s hard to know sometimes what to believe.

    My point is, certain issues should be clear in a relationship – you’re either on the same page or you’re not – but they’re not always. All kinds of issues can muddy the waters and make people hang in there sometimes much longer than they otherwise would, and then it becomes difficult to know when it is fair and appropriate to have the serious conversations and get some answers.

    1. 1.1
      Karl R

      Clare,

      Another dating expert had something she called the “three month checkup” for relationships.  At three months, you should be exclusive and referring to each other as boyfriend/girlfriend.  If not, ask for clarification about what your partner wants along those lines.

      Every three months afterwards, check where you are compared to three months earlier.  Has the relationship moved forwards?  Backwards?  Stagnated?  (From day-to-day and week-to-week, relationships ebb and flow.  But over a three month period, those things should average out and a general trend should be visible.)  If the relationship hasn’t progressed, make an observation about that and seek clarification about what your partner wants in the relationship.

       

      Clare said:

      “Sometimes, things simply don’t come up in conversation. Or, one person avoids or postpones talking about certain things.”

      Steering conversations is a skill.  It’s not that difficult.  If I want to bring up finances, I can start with a story about how my parents view finances, and how my views are similar/different.  If that seems contrived, it’s even easier for me to start by talking about my brother’s attitudes (and his constant get-rich-quick schemes from when he was younger).

      If someone is avoiding a topic, that’s more challenging.  But at a certain point, just address the elephant in the room.  For example, “Maybe this is my misperception, but it seems like time I say something about your family, you quickly change the subject.  Is that a sensitive topic?”

      1. 1.1.1
        Emmer

        Apparently I’m going to be all over this thread. I’m with Karl R. on how you can steer the conversation – my cousin met a guy a week after I met my fiancé, was engaged within a month, and got married (5 months pregnant) five months later. I used her effusive Facebook posts as an opportunity to talk about how getting married that fast is based on a guess about who the person is, not reality, but also to say that I wanted to get married someday (that it is important to me), and to talk about timeline. When another cousin had their fourth kid, I talked about wanting kids and how many. He came into the relationship unsure about the concept of marriage and about kids (but open to both, with the right person), which was a warning sign to me, but everything else was so very good, in terms of how he treated me, that I gave it time and let him know what I needed: that I wasn’t in a hurry, but I wouldn’t be happy with a life partnership that was not a marriage, and I wanted kids.

        1. Emily, the original

          Emmer,

          I’m wondering, in terms of the person who wants less, be it the man or the woman, is that person consciously aware of avoiding serious conversations about the future of the relationship? I’m thinking the answer is probably yes. They’re getting something out of the relationship and will ride the wave until the other person demands more.

        2. Emmer

          @Emily, the original – maybe? Probably? I think in this particular case, both of us were equally interested/invested (with some moments of each of us feeling like the other was ahead of where we were). That’s the hardest part to find, in my experience, and that’s what made these conversations easier for us to have. The question was more whether we both felt a need to have the marriage title attached to the lifetime commitment, and when we were ready to make the lifetime commitment. But one thing I didn’t say before – these conversations are/were a tiny part of our relationship. Mostly, we just like each other a lot, and have a lot of fun together. So one conversation every six months, maybe, over the last two years? I think the one about timing was about when we first said I love you, six months in. And then I forgot about it and focused on enjoying what we had and seeing how I felt about him until something brought it up again, many months later. We weren’t in a rush to figure it out, but we did talk about what the other person wanted for their own future as part of figuring out whether the visions were even compatible. (I was at a point where if someone I dated wanted to be polyamorous or never get married or never have kids or live in the cold tundra, I didn’t take it personally – good for them, not for me. So there wasn’t any pressure on him except that he knew what I needed in the long term if he wanted to be with me.) Again, I do not have this figured out. I got ridiculously lucky. But I am now a huge proponent for owning what you want, and letting the other person decide if that works for them.

        3. S.

          Emily, I don’t think the person is consciously avoiding.  Their mind is just not there. Most people talk about what they are thinking about. That’s why listening is great.  That is usually a person’s internal narrative. I used to think that people hid their real thoughts until they knew you better (’cause I keep my private thoughts private), but that’s not most people, I’ve found. Especially once your are boyfriend/girlfriend. You are in the inner circle!

          If they aren’t saying it or thinking it, that in itself is information to know.  Tells you where they are.  Amy could steer or ask.  She could wait a few months.  But generally, I think by three months (and she said they both were serious) people know if they want a future.  Maybe they don’t know if they want it with this person, but in general people know what they want or don’t want.  If a person doesn’t know?  They usually simply aren’t ready.  Maybe they’ll figure it out, maybe not.  Give it time, but not too much time.

        4. Emily, the original

          S.,
          Emily, I don’t think the person is consciously avoiding.  Their mind is just not there. … If they aren’t saying it or thinking it, that in itself is information to know. 
          I’m just remembering the one time that happened to me. The guy I was dating made it clear, and mentioned several times, that he wanted a serious relationship. He said he was looking at places for us to live. I don’t remember how I responded, but I’m thinking that I said nothing. So I was aware of what he wanted and aware that I didn’t want the same thing and knew I wouldn’t change my mind. The relationship didn’t go on that long, but I should have ended it sooner.

        5. Emily, the original

          Emmer,

          But I am now a huge proponent for owning what you want, and letting the other person decide if that works for them.

          That’s a good way to do it. I think people are afraid to let the other person know what they want because they are worried it will come off as needy or pushy. But it doesn’t, unless it’s delivered way too early in the relationship

      2. 1.1.2
        Clare

        Karl R,

        Yes, I agree there’s a certain skill to steering a conversation in the direction you want it to go, and I agree that it’s not that difficult. If someone seems edgy or avoidant on certain topics, however, it’s not always easy to know how to react. People in relationships will often gloss over unpalatable information or try and massage it into a form that sounds more like what the other person wants to hear, so these conversations are not always satisfying.

        For instance, a man might say that yes, he wants to get married someday but that his parents had a horrible divorce and that he suffered a lot of trauma from that, so he wants to be absolutely sure of making the right decision. That sounds fair enough, but it also leaves the other partner with a whole lot of questions that, if asked, are going to feel like pressure. My point is, at some point, the partner who wants answers is going to have to put pressure on if the other person is not forthcoming with answers. Either that or leave the relationship.

        I think Emily’s point was a solid one that the partner who wants less will consciously avoid or mislead conversations because he or she is getting something out of the relationship and will ride the wave for as long as possible.

        I like the 3 month check in rule. It forces a person to be more objective about their relationship. I might use that in future.

    2. 1.2
      Stacy

      @Clare

      Good points.

      Personally, I am a big proponent of ‘people will do what they want to do’, and especially men.

      Rarely did I come across these issues in any relationship I’ve had. If I am not a girlfriend by two to three months,  best believe that we’ve already had a low stressed,

      casual conversation about it at that point.  So, at that point, I will be dating others and he will just know I am dating others because my attentions will fade.  But honestly, I tend to just leave because when a man wants you, he will make it clear that he wants you.

      There are also so many ways to bring up a conversation and ‘feel’ out another person without directly addressing the question. Does he believe in marriage? Then find an article and ask him what he thinks about it. Tell him a situation and ask his advice, etc.  It hasn’t failed me yet. Then there are times when one must be really direct (for instance, you’re in a relationship and years are going by with no ring). Personally, I will not date a man for more than two years without a proposal. Sorry. You don’t need more than two years with me to know if this is what you want.  I will not nag you. I will simply tell you we need to date other people because I am looking for something a bit more permanent. However, a man would step up if he doesn’t want to lose you. So, there is no way I will be in the position ‘waiting’ for a ring 4,5,6 years. I am late 30s and have no time for that.

  2. 2
    Emmer

    I am by no means an expert on this, but what I found to work in my relationship (that started when I was 36) was to be honest about my expectations and desires when the topics came up, without suggesting to him too early that I expected him to be the one. A lot of it was based on Evan’s timelines, so I would say things like, “well, I read the blog of this dating coach who suggests that three years is about how long it takes to determine whether or not you want to marry someone. It’s not necessarily a hard and fast deadline, but I do want to get married, so if I got to three years and either me or the guy wasn’t sure yet, I would probably seriously reconsider the relationship.” When finances came up, I said, “my parents have changed how they did this over the years, but I like the idea of combining and then each getting a fun money account.” It helped a LOT that I had finally reached the point where I didn’t date anyone I didn’t feel comfortable being blunt about my desires with, and that I am with a guy who has surpassed my expectations every time hard topics come up. But it was all about what I wanted in life, not what I wanted from him. When I turned 38 and felt a few days of way more pressure about kids, I told him that I felt that way, but that I didn’t want to put pressure on him (he’s younger) or myself or the relationship. We talked about what it meant to be sure about a relationship (I said I tried to imagine what would be different in a better relationship and couldn’t think of anything; also that I would feel more sure if I knew that he were sure). Two months later, he proposed. Total surprise. Evan honestly gets a lot of the credit for the matter of fact attitude I had toward the whole thing. I was a slow learner, but I got there eventually.

  3. 3
    John

    Evan said:

    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.

    This paragraph is gold.

    I’ve been on many dates where the woman I’m with starts grilling me on the first date about what kind of home I own, my job and how many kids I want.

    I always chuckle and say, “ask me my favorite color or where I like to vacation.”

    We can discuss hope, dreams, baggage and how many kids we want after the first few dates.

  4. 4
    lisa

    I agree with Evan and my personal experience has been that men who want marriage, children, a home and are financially fiscal bring these things up on their own.  Many men when I did online dating at least brought it up themselves on the first date, or sooner.   Often I did feel like it was an interrogation, but mostly what it felt like was that he was not looking for a connection with me or any person in particular, but kids and a baby mama.  It has a real way of killing things early on.  So I do not think it is just women that do this.  If you meet online though you also have the advantage of most people putting what they are looking for right on their profile.    I think it could make things easier to just not pick men who do not mention these things in their profiles.  But if you are a woman in your 30s and marriage, family and finances are a priority I do think you need to find someway to bring it up at least by the third month.   The reason I say men bring this up on their own, is because my current fiancé did, and that’s what he did that was different than most of the other men I dated.  He did not on the first date, but early enough on that I knew we were seeking the same thing.  Often I think because many women (myself included) have never dated this man, the one that truly wants this with us, we don’t believe that there is a man that will bring this up.    But there are.  I think this goes a long with women who seem to only have ever dated jerks.   After awhile you start to think that that’s how all men are, and you accept less than you deserve, because you meet a man who is slightly better than what you are used to, and think he’s somehow a great guy.  You either never had a great guy or it has been so long since you did that you start to accept less than you deserve.  Online dating fatigue commonly creates this problem.  I am not saying that men online are more likely to be jerks, they are not. What I am saying is that online dating gives you the chance to date a lot  more than you would have otherwise, so you do encounter more  jerks.

    I suspect this writer, like me is a professional who is direct in her work, and assertive.    So if she wants to know something, she asks as did I.  I agree with some of the others that there is an art to conversation steering.  One such is to simply state your wants and needs without asking him h is.  I think if you are two or three months in and you do this, and he becomes nervous or non responsive you may not be with the right guy.   Where Evan and I may disagree a bit is if by month three he has not brought up, and your subtle attempts to steer the conversation are not working, you need to just ask him right out. Not in the manner that you would cross examine someone, but having a direct conversation. I would even mention that it has not come up, and that this is something very important to you and you would like to know.  There are many usually beta men that will not bring this up themselves and those same men and many men for that manner don’t always take hints or innuendo the way women do.   While my fiancé brought things up, when it comes to taking hints he is horrible!  So sometimes you do just need to be blunt.  And if at three months he has a negative reaction, then it is time to move on.   So at this point, if he leaves because you asked this question he’s not your man, and you never really lost anything, because you did not have what you throught you did.  The best thing to do is to watch their actions.  Does he invite you to his family’s home, does he tell his friends about you, do you meet them. Does he talk about kids, is he happy around kids?    There are many men (and women) who will legit lie to keep a relationship going knowing that they don’t want the same things. And there are some men who just really hate conflict and will tell you whatever they think you want to hear true or not.  So actions are really the only way to gauge this, and that of course takes time.

     

    Finally in reading this letter I suspect this writer has some specific baggage from her past, and as noted in the response she is fearful and trying to protect from that.   I say this because she has some very specific statements about living with in laws.  Unless she is of a culture where that is common, it seems quite specific.  we all have this baggage at this age.  But ultimately all dating and love is a game of chance.   You have to get hurt a few times to win, and you cannot prevent that many times no matter how hard you try.  You could be with a man for three years he clearly states he wants marriage and kids, and changes his mind or walks away.   That’s the game of love, but with the lows come the highs and you have to be willing to take the risk.  Strike that, if you do not take the risks you will end up alone.  Good luck!

    1. 4.1
      Clare

      ” There are many men (and women) who will legit lie to keep a relationship going knowing that they don’t want the same things. And there are some men who just really hate conflict and will tell you whatever they think you want to hear true or not.  So actions are really the only way to gauge this, and that of course takes time.”

      Thanks Lisa, you articulated exactly what I was trying to say! Sometimes you have to be blunt, and if in doubt, look at the person’s actions.

      1. 4.1.1
        Nissa

        Exactly!!! Evan even has a post somewhere, I think it was the “My Boyfriend Won’t Tell Me I’m the Most Beautiful Woman in the World” post, which touches on this. He basically said, that when you are telling a man what you want to hear, and he disagrees, that the man just will hide his disagreement to keep the peace. At one point Evan even said something like “you are just asking him to lie to you”. (Apologies if I have not gotten this exactly right).

        But that has been my experience, that most of the time people just tell you what they think you want to hear, not what they really want or believe. I used to do the ‘subtle steer’ thing and found it very lacking. My ex managed to hide a number of behaviors over the years. Most of them were things that he and I had never even discussed, so I know it was not an issue of my being demanding or overbearing – how could it be if we had never talked about those things? He simply had a habit of hiding things he felt would be questionable (or, as one of my good friends said, “he’s a coward”).

        I 100% agree with Clare that you can only go by actions. Now I agree to dates, listen to what he says, listen to what he doesn’t say, and decide for myself.

  5. 5
    John

    I’m the type of guy that would marry a woman with whom I have a deep connection. That deep connection could not be achieved in a few dates. I’m not in a hurry and I’m not dragging my feet.

    I am open to kids with the right woman; not just any woman. Some friends of mine want kids so bad that they compromise way too much.

  6. 6
    Stacy

    Sorry, but 3 months is way too soon to be talking about ‘combining assets’ and the possibility of ‘living with future in laws’.  Gosh, could the guy have the opportunity to enjoy the relationship and REALLY get to know you? At 3 months, it is still the fantasy fairy tale infatuation stage.  You’ve barely been together through a season. You don’t know what he is REALLY like when he is angry, frustrated, sad, etc.  If I was him and a guy started to talk about combining my assets only a quarter of the year since I started dating him, I would sprint for the hills.

    I also agree with Evan. This sort of stuff should come up organically. It shouldn’t be a conversation you would have to interrogate him about.  However, I DO believe that there are certain conversations one should have early (first 3 months). If you are marriage minded, you NEED to know if the other person is.  If religion is important, you need to know if the other person believes in God.  If you want kids, you need to know if the other person wants kids. But all those questions should be able to be integrated lightly and naturally. And,  it costs the other person nothing to answer (as opposed to trying to back me up in a corner on timeframe of combining assets).

  7. 7
    amy klein

    Sorry if the OP is 37 and does want kids (and has not frozen her eggs, ) she’s in a bit of a time crunch for fertility. She needs to get her priorities straight and mention how much she wants to be a mom with the right man. Maybe combining finances is too soon but i think wanting kids and marriage is not.

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