Clear-Eyed Dating — 7 Tips for Dating Success in 2020

As a single relationship therapist in the dating world, I face unique challenges that “civilians” don’t.

I also have a perspective on the whole process that’s different from that of my clients who are also single, since I come at it from both my personal and professional mindsets. I’d like to share with you seven lessons I’ve learned from my time in the trenches, from my clients, from the experiences of the men I’ve dated, and from my single girlfriends.


1) It’s as important to BE the right person as it is to BE WITH the right person.

You’ve probably noticed this in other areas of your life: different people bring out different aspects of our personalities, both positive and negative. There’s the co-worker whose delivery always sounds like criticism to you, so you go into any conversation already defensive, though that’s not how you usually are.

Or, your friend who brings out the goofy parts of you that you didn’t remember were there. There’s the person you always feel protective of, and the one you just want to smack sometimes; the family member who comes to you for your wise advice, and the one you can never please. As it is with these relationships, so it is with dating.

Different people will call out different things from you, so it makes sense to pay attention to who you are when you’re with someone.

Do you like the person you’re being in that moment? Do you feel genuine and authentic, or are you trying to be what you think they want? Are you playing a role, or being a better version of your true self?

We should all strive to have people in our lives who bring out our best selves, and maybe show us aspects of ourselves we’d never seen, or forgotten, or that weren’t there until that person came along and called them forth. Be around people who elevate you, because those are the right people.


2) The right person at the wrong time isn’t the right person. 

Maybe one of you just ended a relationship and you’re not really ready for another, but you meet and it just feels so right. Or maybe they’d be perfect if only they lived closer, or weren’t raising young children when yours are already grown, or weren’t starting a new career when you’re looking to wind yours down.

Whatever the reason, if you’re in a place where you’re available and interested in a relationship, and the other person isn’t, then that isn’t the right relationship for you. Logistics and timing matter, and denying that truth will just make things difficult and frustrating for you both. Life stage differences can be a big source of conflict between two people, and being aware of that can save you both a world of hurt.


3) It’s good to have rules and standards, and it’s OK to break them.

I encourage my clients who are dating to have standards about what they’re looking for, what they’ll accept from a partner, what their deal-breakers are, and what are their must-haves. I find this helps weed through the dating jungle, especially in online dating.

For example, I’m highly allergic to cigarette and cigar smoke, so a non-smoker is a must-have. I can’t and won’t even consider someone who smokes. I have pets, so an animal lover is a must. Other people have other standards, and I encourage that. Think about it…if you’re dating for a relationship, you’re auditioning someone for the job of being your one-and-only. It makes sense to know what you’re looking for, if only to make the field of candidates more manageable.

I have a client who said she’d never date a man much older than she, and not one who didn’t want children.

She was in her early 30s at the time, and wanted to be a mom more than almost anything, so her rules made sense. Much older men would likely have enough children already, and since she was certain she wanted a family, any man who didn’t just wouldn’t work. She was saving both herself and the men from wasting time on something that was going nowhere.

And then she met HIM. Her man. The one she’d waited for, hoped for, talked about, and almost despaired of ever finding. And yet…he was eleven years older, had children already, and was certain he was didn’t want more. So certain, in fact, that he’d had a vasectomy years earlier.

She came to me in a quandary. What to do? He was PERFECT for her in so many ways, but the thing she’d thought she wanted most was out of the question. She could love his children, but they’d never call her Mama, and she so wanted that.

She chose to end the relationship, despite loving him and being loved by him more than she thought possible. Her dream of having children was just too precious to her. Yet, she was miserable without him. Miserable! He was equally miserable, but still committed to not wanting more children, even with her. She and I talked, she cried. He and I talked, he cried. This wasn’t an issue where compromise was possible. Give up her dream of motherhood or give up the man of her dreams?

Reader, she chose him. She realized that she had something amazing, and the possibility of motherhood wasn’t worth giving up the certainty of the love of her life. She grieved, and still does sometimes. He supports her, and feels guilty that he can’t fix this. They work through it whenever it comes up, and otherwise live a very happy life. Some rules are made to be broken.


4) Early on, it’s good to date “an inch deep and a mile wide”.

This is the exact advice I give my clients, and that I used myself when I entered single life. When we end a relationship and start dating, we often don’t have a good idea of what we want, we just know what we had, and what pieces of that we do and don’t want to replicate in our next relationship. We also don’t know who we want to be in a relationship, we just know who we were.

Taking some time to casually date lots of different people can give us lots of good information about who we want to be and what we want in our next relationship.

Serial monogamists, people who jump into relationships quickly, one after the other, often don’t learn much from any of them. They can keep repeating the same mistakes over and over, making the same choices and hoping for a different result.

Take my client who’d been married or cohabitating with a series of women his entire adult life, not having any idea why none of them stuck. We did a deep dive into his choices, analyzing the women he’d been with for similarities and differences, and to his surprise, we found out that he’d been repeatedly choosing the same type of woman, just in a slightly different package. Beautiful, stylish, aloof, wealthy…different versions of the same person. We also did a deep dive into why all his relationships ended, and also to his surprise, he found out that he pretty quickly got bored with them.

He realized that having the most beautiful woman in the room didn’t make him happy if she didn’t also bring something else to the table: intellect, interest, wit, humor, zest for life. To try to change this, we agreed he’d date widely but casually for 3 months, going out with women he might not have considered before because they didn’t meet his physical standards of beauty.

He could still date attractive women, but he needed to look for qualities that would keep his interest, things more substantive and sustainable than looks. He’s still in the process, having fun, and meeting lots of interesting women. Though he hasn’t met his one-and-only yet, many of them have become good friends.



5) Anything that can happen quickly can happen slowly. Red flags are there for a reason.

It can be tempting to run full-tilt into something when we find the “right” one. We meet, we click on so many levels. We feel we know ourselves and what we want, and they check most if not all of those boxes, so why wait?

Well, here’s why. Some red flags are there from the very beginning, but we don’t realize they’re red flags until we see them more than once. Some personality characteristics need to be viewed in several contexts for us to see they’re problematic. The man who gets too drunk on Friday nights with his friends may or may not have a drinking problem, and you’ll probably only know by taking time to watch and learn.

The person who’s snarky and condescending to your server may not be “having a bad day”…you just need to wait and see. Or the person whose life is just “crazy busy” all the time, who seems only to have time for you on their schedule. Are they really that over-scheduled, or are they using it as a distancing technique? You won’t know that for awhile. You’ll need time to see if things just never really settle down, they’re not truly available, and you’ll be left hanging more often than not.

Taking time to really get to know someone gives us the opportunity to see what they bring to the table, both positive and negative, and decide if we’ll be able to deal with the difficult parts…because we’ve all got them.

We also get to see how they deal with our own less-than-lovely qualities. I tend to get snarky when I’m hungry and tired, and I need someone who can suggest I have a sandwich and take a nap, rather than become offended or defensive. I get preternaturally calm in a crisis, then overreact once it’s passed…just when most people are calming down. I need a partner who gets that, and won’t take my under-reaction for lack of concern, nor my delayed response as an overreaction. This is something only time and experience will tell.


6) People should earn your trust, not be given it.

This is a tough one for so many of us. We often go into new relationships giving people our trust, our vulnerabilities, and our belief in their good intentions. We even say things like, “I trust people until they give me reason not to.” The problem is that sometimes the “reason not to” can be so painful it can break us for a time.

Better to invest in someone to the extent they invest in you.

Give them the opportunity to earn your trust by the way their words, actions, and energy match. Offer them pieces of yourself in increments, and see what they do with that. When you tell someone, for example, that you’re terrible with math and ask them to add up the bill for you, do they quietly do that, or do they use it to tease you and shame you?

If you’re having trouble with your sister, do they support you with care, or do they dismiss your concerns? If you bring to their attention something they’ve done that bothers you, do they listen and respond with thoughtful concern, or do they become angry and defensive?

Better to test the waters with your toes than to jump in, not knowing whether it’s calm and warm, freezing cold, or full of sharks.

7) And finally: You can’t fix people. And that’s a painful lesson.

This one came from a good friend of mine. No matter how much glue we bring with us, or how good our intentions, we can’t fix anyone but ourselves. So, make sure that someone’s brokenness (and we’ve all got some, let’s be honest) is the kind you can live with. Choose not only someone’s shining qualities, but also choose what challenges or difficulties you’re willing to deal with. And be honest about your own.

If we want to be fully known and loved for who and what we are, we have to be willing to let ourselves be seen, heard, felt, and understood. Which can be hard. And scary. And sometimes painful. But it’s the only way to live whole-heartedly. To quote Brené Brown:  “Because true belonging only happens when we present our authentic, imperfect selves to the world, our sense of belonging can never be greater than our level of self-acceptance.”

Here’s to us all finding and keeping love that we deserve, and being the love someone else deserves and wants to keep!