Month: April 2025

Discerning Who You’re Looking For

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A lot of us mid-life singles have a clear idea of what we seek in a romantic partner and relationship. To that end, in my last post, I explored the efficacy of using a checklist of desirables for a romantic partner as a general guide to navigate with, rather than a rigid rulebook of must-haves that limits you out of relationship.

But what if you’re newly single and still getting oriented to your new milieu? What if you don’t know what you want in a romantic partner? What if what you’ve been doing and who you’ve been dating hasn’t worked out so well for you? What if nothing much is happening in your love life? Are you willing to open yourself to new possibilities? If you’re not sure who you’re seeking or you’re willing to reconsider who you might be open to, then this post is for you!

Let’s consider how you can better orient yourself to navigate in the direction you want to go, even if you don’t know which way that is yet…

Patterns of Attraction

If you don’t have a sense of who you’re looking for at all, it might be helpful to reflect on whether you have any patterns of attraction to certain qualities or types of people. Consider past relationships, dates, interactions, and dating profiles. Do you see any patterns of attraction in your dating and relationship history? Are there any qualities that you find enticing or are drawn to?

These qualities may be:

  • Physical Traits: height; ethnic heritage; skin color; eye color; hair color/style; body type…
  • Personality Traits: confidence; sense of humor; carriage; intellect; generosity; thoughtfulness; punctuality; introvert/extrovert…
  • Type of Career/Profession: artistic/creative; scientist; pilot; medical; military; education; technical; entertainment; financial…
  • Perspective: politics; religion…
  • Lifestyle: urban; outdoorsy; maritime; rural; social; travel…
  • Talents: musical; artistic; writing; woodworking; cooking, athletic/sports…
  • Recreational Pursuits: surfing; sailing; equestrian; hiking; running; skiing…

After a few years of post-divorce dating, I realized that I was dating a lot of men with a Mediterranean heritage–specifically Jewish, Greek, and Italian. I’ve also dated a lot of creative/artistic men. I don’t limit myself to such men, but I learned to recognize that those are attractive qualities to me, giving me a self-awareness which has empowered me in my romantic search.

Similarly, my friend Leah, who remarried a couple of years ago, remarked to me that all of her significant romantic relationships, including both husbands, were men of Irish descent. A little uncanny for someone outside of Boston, and definitely a pattern of attraction.

My hairstylist’s two most significant romantic relationships were both with engineers. Coincidences such as this are generally more than simple serendipity. For some reason, she’s been drawn to engineers in her past. Do you see any patterns of attraction in your relationships and dating history?

If you can’t pinpoint any particular patterns yet, pay attention to this going forward, as you look at dating profiles and go on dates. If you find a particular profile or person attractive or intriguing, what is it about them that draws you in? Their piercing eyes? Their sense of humor? Their active lifestyle? Be attuned to any patterns.

Once you identify some qualities that resonate with you, you can use that as a general guide to help you navigate the dating landscape. Recognizing such qualities doesn’t need to limit you to those qualities. Rather, use that awareness to empower you in your search for a suitable and attractive romantic partner.

The Rearview Mirror

Besides having an awareness of what qualities you find attractive in a romantic partner, it can be helpful to look back on your past relationships and dating history to analyze where you’ve been–what has worked for you in the past, as well as what hasn’t worked. You can use this knowledge to help you recognize good potential partners and steer clear of bad situations.

What Worked

When I started dating again post-divorce, I was surprised after a year of multiple misfires to find that I was attracted to the same kind of man mid-life that I was in college. My college sweetheart was a tall dark handsome art history major with a playful sense of humor. Isaac, the first man who really made me swoon in mid-life, was a Jewish (check: tall dark handsome) art museum director (check: art type) and is one of the funniest men I’ve ever known (check: sense of humor).

Recognizing these parallels was a powerful light bulb moment for me. Going forward, I was able to avoid wasting time on men who couldn’t sustain my interest and focus my energy on the kind of men who could. Ever since, I’ve been able to up my dating game, dating men who I’ve found more intriguing and who’ve better suited me.

To find a suitable partner as you go forward, begin by looking in the rearview mirror. What qualities in a partner have worked for you in the past?

What Didn’t

Conversely, consider what hasn’t worked out for you in the past. Do a Relationship Autopsy on your big relationships. Why haven’t they worked out? Be honest about owning your role and make note of any patterns of behavior in your former partners that was problematic. Going forward, you can attend to your own shortcomings and be on the lookout for problematic behaviors in potential partners.

If you see any unhealthy patterns that you’ve manifested in the fallout of your relationships, then be attentive to that and do the work you need to do to ensure more success in the future. I’ve certainly done a lot of work toward being the best version of myself that I can muster at any given time, as well as to be the best romantic partner that I can be. In a relationship, it’s crucial that both partners are working toward that end. If the bulk of the emotional work of relationship falls to one person in the relationship, that’s a setup for failure.

If your romantic partner didn’t or doesn’t do their best to be their best self and partner, then there’s nothing more you can do. That’s their shortcoming, and it limits the potential for the relationship. You either live with it, or you move on and learn from it.

My Story

In my marriage, there was a lot of drama. When my ex and I disagreed, he was condescending and dismissive of my point-of-view. We didn’t need to be in disagreement for him to be dismissive of my feelings. I knew that I deserved to be treated better, but while years of emotional and verbal abuse made me resilient, it also made me emotionally vulnerable.

With Stanley, once again, my feelings were frequently dismissed. He prioritized his ex’s needs over mine. He promised much, but his actions failed to follow through. So much of our relationship never made sense to me, yet by staying in the relationship, I was at some level accepting the situation, because I was accepting a partner who treated me that way.

Eventually, I got fed up with being in relationships where my feelings were marginalized and I was mistreated. I knew that I deserved better, but it was up to me to reject worse and claim better. I couldn’t do that within the contexts of those relationships, because the partners I was with had limitations.

What I learned from these relationships forms the basis of my Relationship Values–how I want to feel in relationship and what I want in a romantic partner. These days, I pay close attention to how a man makes me feel; whether I feel seen and heard by him; whether his words match his actions; and whether or not a situation makes sense to me. If I want to have a successful relationship, I need to choose a partner who’s capable of being the kind of partner I seek.

Kate’s Story

My friend Kate, reflecting on her dating history, realized that she’s dated a lot of “Assholes”. Essentially, that translates as men who haven’t treated her well or made her feel valued, often amounting to them blowing her off. She may have liked them, but she didn’t like the way they made her feel. Having an awareness of this, she’s developed an Asshole-radar which she pays close attention to.

Your Story

Looking back on your relationship and dating history what are the big red flags that you see in the rearview mirror? What were the problem areas of your past relationships? What faults and characteristics of your past partners caused you so much grief that you want to steer clear of them in the future? What are your relationship values?

Try to be as specific as possible. The more clarity you have on what doesn’t work for you, the more easily you’ll be able to recognize those shortcomings and behaviors when you see them.

Final Thoughts

Having an awareness of your patterns of attraction, as well as characteristics in partners that have and haven’t worked for you in the past, allows you to be more intentional in your search for a suitable romantic partner. Work to be your best you and know what does and doesn’t work for you, so you’re ready for that right romantic partner and recognize them when you see them!

May you find the partner who’s worthy of you. Good luck out there!

Up Next: Shifting Dating Strategies to Match Your Phase

Use that Checklist as a Guide, not a Rulebook

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Except for those among us who are freshly single after years off-market (and still orienting themselves to their new context), most of us singles have a sense of what we’re looking for and attracted to in a romantic partner. The longer we’re single and oriented to this gig, and the older we are and have a strongly developed sense of ourselves, the more we tend to settle into a sense of the kind of romantic partner we want and who suits us.

This sense of what we seek in a romantic partner often takes the form of a mental checklist of qualities, characteristics, desirables, and/or must-haves. While such a checklist can be a helpful guide, keeping us from expending too much time on poor matches, if a checklist is too rigid, it may prevent us from meeting our ultimate goal of relationship and right romantic partnership.

The Role of a Checklist

The purpose of a checklist should be to help you find a suitable romantic partner, not rule good potential partners out. To that end, be careful how you use your checklist so that you don’t prematurely dismiss a great connection.

The abundance of profiles that come with online dating can amplify the propensity to be dismissive of potentially good matches. It’s okay to be picky, but if you truly seek relationship, at some point you need to pick someone rather than succumb to the paradox of choice. And with luck, they’ll pick you too.

So, how to use a checklist productively? Let’s explore…

Re-Purposing that Checklist as a Guide

Think of your checklist as a GPS, steering and navigating you to where you want to go, in this case, to a romantic partner. The purpose of GPS is to help you arrive at your destination. When you plug in your destination, sometimes GPS gives you alternate routes to choose from. But those aren’t the only routes to your destination, GPS is simply trying to find your best options. Sometimes, I go off-route and GPS has to catch up to me and reconfigure my route. And sometimes I do that romantically as well.

Furthermore, there are plenty of destinations worth visiting, not just one. So, why be rigid about one route to one destination? Let’s expand our navigation options, so we can find a suitable destination rather than limiting ourselves from the get-go.

Breaking Down the Checklist

The checklist is to help you discern good candidates for relationship, but if you give equal weight to all items on the checklist, it works more as a rulebook, a binary yes/no in/out scenario, potentially dismissing good possible mates because they don’t fully measure up to a perceived ideal. But Ideal isn’t real, and holding out for it is a pointless endeavor. Reality is where we live. To keep it real, look for the real person whose preciousness you can appreciate, despite their imperfections.

To re-envision your checklist as a guidance system, you need to breakdown the items in your checklist. Consider each item a guidepost to help you get where you are going, and keep in mind that some signage is more important than other signage.

Must-Haves vs. Preferences

Consider the qualities you find attractive in a partner–physical looks, personality traits, values, education level, politics, faith, career, sexuality, location, etc. What are you drawn to in a partner? What do you want? What do you need? What turns you on?

Must-Haves

Now, breakdown those qualities into must-haves and preferences. Must-haves are the qualities that without them are dealbreakers. These are qualities that are so important that you can’t envision relationship without them. The nature of these qualities has different weight for different people. You get to decide what your must-haves are.

While it’s important to define what you must have in a relationship/romantic partner, try to keep your list of must-haves small. The longer and more rigid this list becomes, the more narrow your pool of possibilities and potential matches becomes in turn.

Preferences

Preferences are those qualities that are inclinations, turn-ons, and desirables. Knowing your preferences can help you identify good potential matches, and by not qualifying them as must-haves, you allow wiggle room for flexibility, the wonderment of the individual, the person who surprises you, and the exciting expansiveness of possibility.

For Example

In my years as a single, I’ve discovered that I have a strong inclination toward men of Mediterranean descent. I’ve dated a ridiculous amount of men who claim a Jewish, Italian, or Greek heritage. That’s a preference but not a must-have.

However, physical attraction is a must-have for me. If I don’t feel physically attracted to a man, then I don’t see the point of exploring the connection. It just so happens that I find a lot of men of Mediterranean descent particularly physically attractive, but Mediterranean heritage doesn’t account for all of the men who I find physically attractive.

A friend of mine has a very particular sexual proclivity. For him, this is a must-have in relationship. It’s a very specific and strong inclination that’s important to him. This proclivity narrows down his pool of potential mates dramatically, but it’s important enough to him that he opts for that.

Different qualities have different importance for different people. For some, religious faith is an important must-have in a partner. But if that must-have takes the form of a specific denomination, that narrows someone’s options significantly, rather than allowing some wiggle room in what form that faith can take. As you think about your must-haves, consider where you can allow for that wiggle room.

You

You get to decide what your must-haves and your preferences are. Knowing both can help you discern good potential romantic connections, and limiting your must-have list will help keep your possibilities open. The more you limit your must-haves, the more you open yourself to possibilities. Conversely, the longer and more specific your list of must-haves, the narrower your pool of possibilities becomes.

Turn-Offs vs. Dealbreakers

Much as must-haves and preferences can help you discern a good potential romantic partner, turn-offs and dealbreakers can help you avoid wasting overmuch time on individuals who aren’t a good fit. To return to the GPS analogy, turn-offs and dealbreakers help you navigate away from dead-end roads and avoid plugging in a destination that’s not where you really want to go.

Turn-Offs

A turn-off is anything that is an undesirable or less than ideal quality, but not necessarily a dealbreaker. Pay attention to turn-offs, they rightly give you cause to pause, but if the person has enough attractive qualities, consider whether the connection is worth further discernment. After all, we’re all imperfect. In the larger context of the individual, is the turn-off potentially negotiable for you?

Dealbreakers

A dealbreaker is a quality that you feel so strongly about that you can’t even entertain the idea of relationship with someone because of it; it’s an absolute with no room for negotiation. As with must-haves, the longer the list of dealbreakers, the more your pool of possibilities narrows.

For Example

Damon was a smoker. A turn-off for me, but I liked Damon more than I disliked his smoking. Ideally, I’m not looking to get involved with a smoker, but I made an allowance for him because I really liked him.

Paolo has multiple marriages and divorces in his past. I’m a divorcee myself, but multiple marriages/divorces always gives me pause. That said, he has many qualities that outshine this aspect of his history. And we all have histories. His history is part of him, but it doesn’t define him. With Paolo, I choose to look beyond the history and see the man he is now.

I was enjoying getting to know Jay, but when he disclosed that he’d be celebrating the Christmas holiday with his ex, that was a dealbreaker for me. At this point in my life, I won’t get involved with a man who can’t leave his past in the rearview mirror. Been there; done that; can’t do it again. That situation was an emotionally turbulent experience that I don’t care to revisit.

You

When defining your dealbreakers vs. turn-offs, consider which are absolute non-negotiables and where you can allow wiggle room for the right person. What are your limits and where can you be flexible? We’re all imperfect; what imperfections can you allow for? As with must-haves, the longer the list of dealbreakers, the more your pool of possibilities narrows.

A Spectrum vs. a Binary Perspective

As you sort through your must-haves vs. preferences and turn-offs vs. dealbreakers, envision it as a spectrum. At one end of the spectrum is the must-haves and at the other end, the dealbreakers. If one is white and the other black, everything in between is a gradation, mostly gray.

This is where we live, the messy gray. Life isn’t a clear-cut simplistic binary endeavor. Life’s complicated, and so are people. Where on that spectrum are you going to draw your limits? How broad are you going to keep your spectrum of possibilities?

Seeing the Person Behind the Profile

Behind each profile is a real person. Okay, except for the bots and fake profiles which are an unfortunate annoyance with online dating…but for the most part, the profiles represent real people, individuals with stories, histories, successes, and failures.

Profiles are a watered down version of the real person. Some people have nothing to say in their profiles–they literally (I’m an English major–I’m using that word correctly.) don’t write anything in their profile. Such profiles don’t promise much for the person behind them. But, when you find someone whose profile resonates with you, explore that.

Embrace exploring the nuances and substance behind the photos and bio blurb. Try to keep any flaws, imperfections, and turn-offs in perspective as you discern the person and your connection (as long as they hit your must-haves and you don’t encounter any dealbreakers). Allow for the preciousness of connection, when you feel it.

That checklist we each have serves us best as a guide, not as a rigid prescribed route. Have fun exploring off-road, and be mindful of recognizing the person who you want to lock in as your destination despite what may or may not be on your checklist.

Here’s a paragraph from my Match profile that goes to this:

I am looking for someone that I have a genuine connection with, who is sincerely looking for a someone special in their life. Someone who, if we are lucky enough to find each other, is willing to look up from his checklist (if we are connected the things on the checklist stop mattering) and see me looking back at him, and who is willing to follow it and take a risk, despite our mutual imperfections.

Final Thoughts

You get to decide what you need and what your limits are in a romantic partner and relationship. As you determine those needs and limits, consider where you’re able to be flexible and allow room for the nuances of the individual. The broader your spectrum of possibility, the more likely you are to find someone.

Good luck navigating to your destination!

Up Next: Discerning Who You’re Looking For