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What are dating milestones?

A single friend in his early 20s asked for examples of dating milestones based on the previous post. He understood what not to do much better than he understood what to do. As often is the case for ambiguous topics, it’s often easier to define the negative rather than prescribe the positive. And in giving prescriptions, there’s a backlash because not all <fill in the blank> are like that, there’s individual personalities and background, and then there’s situational context. Given all this, I will still attempt to bring clarity to dating milestones. 

Possible dating milestones: Here is a list of dating milestones that I recall in sequence for how my relationship with my wife progressed. We met in college through the ministry of a campus Christian group, now known as Cru. College is such a great place to meet people: similar intelligence and work ethic, often similar backgrounds, shared interests, lots of free time, and no adult supervision or responsibilities. The following milestones could also apply to someone you meet in-person, starting out as friends:

  1. Repeated in-person interaction in group settings

  2. Serve, live or work together - see each other in a stressful context or over time

  3. Repeated 1:1 in-person conversation (text and messaging counts too)

  4. Mutual self-disclosure of family background and other personal sharing

  5. First Define-the-Relationship (DTR) conversation with shared expression of interest

  6. Meeting parents & other family members 

  7. DTR convo about going public (“Facebook official”) and relationship goals

  8. First fight

  9. Spend extended time with friends & family (multiple meals or taking a trip together)

  10. Repeated discussions about marriage

  11. Ask dad for blessing on marriage

  12. Propose!

For the above, the 1st step took two years. Steps #2-4 took a year when we lived in the same dorm. #5-9 spanned 3-4 months. And then #10-12 took about a year. From first meeting to engagement was just under 4.5 years but over three years was the friendship phase.

Meeting through a dating app

  1. Repeated messaging through app/text

  2. First in-person meeting

  3. Repeated 1:1 in-person conversation (text and messaging counts too)

  4. Mutual self-disclosure of family background and other personal sharing

  5. First Define-the-Relationship (DTR) conversation with shared expression of interest

  6. Repeated in-person interaction in group settings (meeting each other’s friends)

  7. DTR convo about going public (“Facebook official”) and relationship goals

  8. Meeting parents & family

  9. First fight

  10. Spend extended time with friends & family (multiple meals or taking a trip together)

  11. Repeated discussions about marriage

  12. Ask dad for blessing on marriage

  13. Propose!

The challenge of meeting through a dating app is steps #1-5 can happen rapidly, in less than a month. And that makes the transition to steps #6-8 very challenging. It’s a chicken and egg problem. It’s difficult to facilitate group activities without some combination of shared values, ease of logistics (same circles/proximity), mutual friends, or shared interests.

What are significant friendship milestones? 

It’s important to consider that many dating milestones are common to all types of relationships. What’s challenging is many of us are just bad at friendship in general. I’m guessing many of my peers have trouble making friends in our forties. We have our inner circle (or friends who have been part of our inner circle). And that circle hasn’t really changed for years, sometimes decades. It’s especially true for married men with children. Once we have children, there’s social pressure to cut off your male friends in favor of being an involved and evolved dad who attends all their kids’ sporting events, graduation, etc.

First, it’s knowing someone in a group context. And the next milestone is knowing them in a different context. For instance, I met Kyle (name changed for privacy)  through a CrossFit class I attended twice a week. I’m terrible at CrossFit and I would avoid working out by asking questions and mingling with other people in the class. That’s how I got to know Kyle and we were some of the few people who would stick around after class to chat. That’s how our context shifted. He started to share about more personal aspects of his life and we went out for dinner and drinks one night. That’s a second context shift. Later, this friend joined a Bible study with me and some other guys from my church. That’s a third shift. It’s important that these shifts are not solely biased towards one person’s context. It’s not just the other person moving into your territory but also your willingness to enter into theirs. It’s mutual, gradual, and reciprocal.

Milestones for the 5 Aspects of Knowing a Mate: Compatibility, Relationship Skills, Family Background, Relationship Patterns, Character & Conscience

Compatibility: What do you like about this person? The longer the list, the more you know the person. It’s a milestone if you can rattle off 3-4 specific qualities (with an accompanying story of seeing the quality in action) without having to think much about it. What shared values do you have? Again, you should be able to rattle 3-4 values that are really important to you that you both share. If you can’t, then you need to talk it over with a friend. And then of course: What do you not like about this person? OR What bothers you? If you can’t think of anything, you’re deceived. If you can name a number of things specifically with supporting evidence and you don’t cringe, you’re likely in good shape. 

Another simple milestone for chemistry is after five conversations, you leave each other with a persistent sense that you want to keep the conversation going. 

Relationship Skills: One significant milestone is making your dating relationship public. There are stages to this but I advocate advancing through them quicker and sooner rather than later. 

I don’t fully understand why dating couples keep their relationship private. This seems to be the case in many Asian churches where couples fear shame and judgment, especially if things don’t work out. I think it also means they don’t want to have to answer questions about their relationship and be joked or gossiped about. 

One challenge is if a dating relationship is made public too soon, there’s social pressure to make it serious. Well-intentioned questions from peers can trigger anxiety. This is especially true in church settings - where it’s everyone’s business to be in your business. 

However, I’m not a private person and value honesty and openness. Therefore, I consider it a yellow flag if someone is not forthcoming about their relationship status (see example below).  I tend to see social pressure as helpful. I welcome people’s questions and I recognize most people are just trying to make conversation when they ask about who you’re romantically involved with. More importantly, I have trusted mentors whose counsel I weigh heavily. The rest I try to brush off and not to take too seriously. I also recognize it’s easy to get “in your head” and obsess about a dating relationship. Keeping things open with others helps me get out of my head.

Another time-tested, socially accepted milestone is your first fight. How you argue and navigate conflict is an important indicator of relationship skills. Who started the argument? How did it end? Who apologized first? Fights are really important. Disagreement and conflict are crucibles of character and invitations to intimacy. You need to fight well.

Many relationship skills are easy to assess even at the beginning of a relationship. Who does most of the talking? How good of a listener is she? How much does she open up personally? 

Family Background: Meeting your significant other’s parents is a time-tested, socially accepted dating milestone. I remember my first time meeting Judy’s parents at her college graduation. That was fun. I could observe the family dynamic. Observing the sibling dynamic is also important. Estranged parent relationships are tough. In these cases, I recommend asking questions about how they navigate those relationships today. You can learn about a person by listening to them talk about their parents and what they say (or don’t say). 

Relationship Patterns: This is the “Let’s talk about our past relationships” series of conversations. This doesn’t happen out the gate but the milestone is when you observe how the person’s past relationship patterns affect your current relationship. There’s an a-ha moment that comes when you understand what a person was talking about. She had kept her last relationship secret from many people. That’s not a good sign. I could tell Judy broke through negative patterns when she talked about me to her friends.

Character & Conscience: It’s possible to fast-track the other areas but this one takes the most time. You need to observe the other person in a difficult situation. Before we started dating, I watched Judy go through a break-up and handle some leadership transition during college. I also knew her friends who spoke highly of her character. This is likely the most challenging aspect to observe in an online dating context. You do this by getting to know a person’s friends. One great way character & conscience is through spending extended time together OR navigating a stressful situation. 

One big milestone is to become acquaintances (on good terms) with at least one of her friends. If that doesn’t happen, it’s not a good sign for the long-term. If you get married, you’re likely going to spend time together with her friends. The same thing applies to you - it’s great when your girlfriend gets along with your friends. 

Shared Meaning in Milestones

Milestones are culturally specific. What makes them meaningful is specific to a set of cultural values. Unfortunately, today’s dating/non-dating environment fights structure and the shared meaning defined structure entails. The price of autonomy and personal fulfillment requires meaning to be negotiated. For example, living together before marriage is extremely common and seen by many as a significant dating milestone. However, one partner (typically the woman) may see cohabitation as an indicator of their partner’s increased commitment and a movement towards marriage. However, the other partner (typically the man) may see cohabitation as a way to reduce rent and have easier access to sex. For one person, introducing a significant other to their parents may be a tremendous milestone. For another, it may be almost meaningless. Therefore, in this dating wilderness, it’s important for a couple to discuss which milestones are significant and the shared meaning in them. 


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