Dating as older adults: Do we risk showing up & asking the important questions?

dating for older adults, relationships, communication

Dating as older adults: Do we risk showing up & asking the important questions?

Dating as older adults isn’t easy. In some ways, as we age, I think it gets a bit harder. Having recently seen the unexpected end of a relationship that seemed to hold potential I am again wondering how we can do it better. Or smarter, in the sense of being present to our deep knowing about who we are and what we want.

If we want to be in a romantic relationship with someone we have to go through all the stages—the awkward meet and greet, the initial euphoria, and then the adjusting phase. That moment when one or both parties stop being on their best behavior and it’s time to figure out the practical aspects of building some form of a partnership with this other person. Or walking away.

In determining what went wrong in my recent relationship, I’m exploring the basic issues we need to consider in building a strong, satisfying relationship. What kind of relationship do you want? Do they want? Are you both committed to spending time together to get to know each other? What mutual likes and interests do you share? Where do you disagree and how significant is it? Do they listen you? are they supportive and interested in your life, or simply expecting you to be there when it suits their schedule? These basic topics can make or break a relationship.

We assume that both parties looking to meet a potential partner are eager to have conversations about what they hope for. To talk about what a future might look like together is a topic for two people. If we don’t ask the questions because it feels ‘forward’ or too direct so early in the game we may be disappointed when that other person isn’t what we had hoped for.

A more nuanced problem arises if we try hard to make ourselves seem desirable, when we try so hard to be the ‘right’ kind of woman, not the woman we really are. We don’t always keep our wants and needs front and center in starting new relationships. We try to be pleasing; it’s what we are taught to do as women. That’s one of my challenges. My old habit was to become more appealing, less of a strong personality. I would play small. And as a consequence I tolerated things I really didn’t enjoy or what in a relationship.

How do we fully show up? Being aware of our tendencies is a good first step—and catching ourselves when we fall back into old ways. I caught myself this time, recognizing he didn’t show the consideration as I deserved. Moving forward I want to seek a balance between being too quick to judge and allowing room for possibility. I think that’s part of the problem many older women experience—a sort of panic at being passed by, at feeling not pretty enough, or young enough, or thin enough. As a result women may feel pressured to grab what’s presented to them, even when that person is not who they envisioned.

Learning boundaries and setting expectations of how we expect to be treated is vital.

The question that arises for me is how to figure out what works when it comes to character traits and politics and emotional availability. By the time we begin dating as older adults we have probably developed fairly entrenched patterns. Accommodating someone new requires compromise and conversation. Finding mutual ground is essential. We have to know what we absolutely will not tolerate and where we are willing to adjust.

Do  you know what you do or don’t want? How can you determine if a potential partner falls in line with your desires for a partner?

I suggest being open and honest about what you want, right up front. Talk about the things that matter to you. Ask questions. Go beyond the meaningless chatter.

What would that look like? I’m not sure yet but I intend to be a bit more inquisitive and revealing next time around. While it feels a bit pushy to ask about their relationship goals on a first date it’s important to be clear on what you seek. The level of comfort they feel as you do this, and their willingness to be open as well will tell you a lot. Defensiveness, evading your questions, being uncomfortable with an outspoken woman provide additional hints at their future behavior. And the more one knows the easier it becomes to move forward.

The best relationships are ones in which we feel heard and supported. The ones where we can be ourselves, show our vulnerabilities, our strengths and weaknesses, and know that our partner is able to care of all the parts of who we are.  This requires us to show up. Remember not everyone can handle who we are and that’s OK too. Who wants to be in a relationship, of any sort, with someone who isn’t fully committed to supporting us in our quest to live our best lives?


Or you could just whip out this list of questions and see how it goes. Ha ha… because I’m pretty sure asking about favorite salty snacks isn’t likely to sway me.

You might want to check out this Q&A from a woman figuring out how to attract the men she wanted to date.

Photo by Prescott Horn on Unsplash

  • Stella Fosse
    Posted at 11:31h, 04 September Reply

    Hello Walker, thank you for this brave reflection. Thanks especially for acknowledging the importance of bringing our full selves to the table right away. The end of a relationship is difficult at any age, but it can take on more of a charge when the time left to connect and the available choices come to seem more limited..
    For another perspective, the relationship chapter in Ashton Applewhite’s book, This Chair Rocks, includes some intriguing ideas about expanding our concept of relationship – way too early right now, but perhaps worth a look later. In the meantime, please take excellent care of yourself.
    All the best,

    • Walker Thornton
      Posted at 09:50h, 05 September Reply

      I’m a big fan of Ashton’s work, will have to go back and reread that chapter. This relationship, as you note, was definitely a reminder for me to hod onto the things I value and center myself in relationships. Fortunately it was an easy ending, in some ways, as I saw it coming and allowed myself to let go and move on. It’s always a learning experience and I’m grateful for those!

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