A mature man and woman sitting on a couch having serious dating conversations.

When To Have Serious Dating Conversations

01 August 2024

Imagine you meet someone you like on a date. You start seeing each other fairly regularly, spending time together a couple of times a week. You feel yourself getting excited about this relationship and its possibilities. It could be getting serious. Is it time to DTR (Define the Relationship) or is it too soon? How do you know when to start having those serious dating conversations about each of your true intentions?

First, let’s consider how you met this person.

Believe it or not, how you met is crucial in determining when to have these serious dating conversations. With online dating, you start with more information about your date than you would of someone you met organically. Ideally, you are communicating intentions in your online profile and looking for dates who are on the same page. In this case, you can approach the subject earlier, to confirm that you both want the same things.

However, if you met your partner through a more organic route, it would be prudent to take more time. Someone you met at an event or in a public space is still a mystery. Even being introduced through friends and family doesn’t guarantee you’ll have enough information to go on.

Once a clear attachment is established however, I recommend discussing your life goals fairly quickly.

One of the biggest relationship problems for those who are marriage-minded is dating someone for six months plus, only to find that they do not want the same things out of life. You spent all that time to discover they aren’t interested in marriage (or kids, or family, etc.). Then, where does that leave you? Especially if you are older or a woman who wants children.

I remember dating one guy that I really liked. Three months into the relationship, I started talking about children. He said, “You want babies?”. I admitted that I did. He told me he was done having kids as he had a few from previous marriages. I chose to leave the relationship in favor of looking for love that included my goal of having a family. I wish I had known sooner so I wouldn’t have become so attached to him.

One of the next guys I dated also seemed Motivated to Marry. We talked about wanting to get married and have a family on our 4th date! It all seemed very natural for us 40-somethings. But as it turned out we had very different ways of practicing our religion. He was expecting me to conform to his ideals, which were very different from how I was raised. Our visions of how our family would be involved in our religious community were not aligned and we agreed not to date any longer.

Having these serious dating conversations is important no matter how old or young you might be.

One of my Boomer clients was a retired woman living in DC, enjoying a full life of culture and friendship. She began dating a man who clearly liked her. However, he spent half the year away, living in Florida in a community that didn’t appeal to her. She couldn’t see herself living that life, going back and forth, leaving behind her DC friends, family, and interests. So, while there was true affection there, they broke up amicably.

Another one of my clients was a man in his early 40s. He wanted to get married and have natural children of his own. He was not interested in adoption. However, he was open to IVF or using an egg donor if need be. When he met his now-wife online, he quickly tried to discern if she too wanted marriage and a family. By checking her profile and reading between the lines of their correspondence he felt confident that he knew her intentions. He brought up what a potential future might look like for them, within just a few dates! As it turned out, she was on the same page and it wasn’t long before they were engaged and married!

When it’s right, it’s right!

When I met Alan (my now husband), I let him know within our first month of dating, that my goal was to meet someone who wanted marriage and family. We had been on a bike ride down the Crescent Trail from Bethesda and were having dinner at the Georgetown waterfront on a summer evening. When I brought up the subject of marriage and kids, he said he was looking for that too! Since we were both in our 40’s there was an understanding that I was not interested in just dating for fun, that I wanted a serious relationship- a marriage-minded relationship. We fell in love fairly quickly and as it turned out, he proposed by the end of December, and we were married the following July!

I encourage you: don’t be afraid of having these serious conversations fairly soon in your dating time together.

Whether it’s about wanting marriage, having children, faith & community, or what a retired life might look like- if something is important to you, especially if it’s a deal-breaker, don’t delay. The right person won’t flinch and will welcome the conversation.

The early stages of a relationship can be both exhilarating and nerve-wracking, especially when it comes to having those crucial conversations. Remember that by being open and honest about your intentions, you’ll save yourself from heartache later on. Don’t shy away from discussing what truly matters to you. By setting clear expectations and understanding your partner’s desires, you can build a solid foundation for a lasting relationship that fulfills both of your dreams.


If navigating dating and new relationships is becoming confusing or frustrating, it’s probably time to take my quiz at www.mtmquiz.com and discover what your dating process might be missing.