5 Things to Stop Doing When Dating

A few weeks ago, when I was back home in CT, I was on a hot date. I was the third wheel on my sister and brother-in-law’s dinner date 🙂. 

I was unloading about my recent breakup all evening because it was very fresh. I’d quickly gone from feeling hopeful, grateful, and excited, to sad, angry, lonely, and confused within a few days of seeing my sister - and she graciously listened as I popped off. 

She commented on how well I do at being single; how independent I am. That is true. But so is the reality that being alone most of the time is highly overrated (kids don’t count), and it’s bad for our health. Human connection is a basic human need. It’s crucial to our mental health, and long-term well-being. We need it, and we all want it for good reasons.

Enter dating which can provide all sorts of fun opportunities for great connections of all kinds! At the same time, when you have bad dating experiences, it only intensifies the loneliness or frustration you’re already feeling. Dating has only grown more complex with polarizing beliefs, evolving technology, changing needs, various relationship structures/philosophies, more transmittable diseases, and the false notion we need to perfect ourselves before entering a relationship.

I’ve learned a lot over the last several years through my clients, and in my own experiences…well…because I’ve dated a lot!  I’ve dated multiple genders, older, younger, as an ethically non-monogamous person, monogamously…I’ve dated during covid with video only, I’ve dated on all the apps, and I have met people organically, through events. You name it, I’ve done it.

I’m still searching for love myself, but here are a few of the important things I’ve learned to NOT do fast, and that have helped me along the way. Stop doing these if you want a better dating experience.

Taking Safety Lightly

As I write this, my brother-in-law and I had a bet about whether or not “Conor” was cat-fishing or dangerous since my intuitive spider senses were going off when we matched on an app (ummm…my intuition was right). Having a clearly defined safety screening process that includes physical, sexual, and emotional safety is critical for well-being, builds confidence, AND creates a positive dating experience for everyone, which is what we all want, right?

Years ago, I was afraid to proactively talk about safety. Would I seem silly, would I ruin my chances with them, would they think I’m crazy? NO. Over time, what I realized was:

1️⃣ Self-advocacy boosted my self-esteem

2️⃣ The conversations got easier

3️⃣ Knowledge is power

The questions & practices literally saved me from harm many times. What a turn-on to have someone openly communicate where they work, who they are beyond their first name, when their last STI screen was, and where they stand on reproductive rights. How empowering to speak up for yourself, and prevent harm. A good starting point is coming up with a list of safety concerns, followed by proposed questions/practices that would make you feel safe engaging with the person, and finally, deciding how you’d get the answers to those questions ahead of a meeting.

Perpetuating a Negative Narrative

We’ve all done it, and we all have at least one story whether it’s “all men in ____ suck”, “ I’m not good enough”, or “no one wants a divorced single parent”.  We tell ourselves, and everyone else this story when things go badly, and unconsciously make it a self-fulfilling prophecy. The process goes something like this: you have a series of bad interactions on the apps, a date that goes poorly, followed by a few month’s relationship that seems amazing, but then abruptly ends - so you discuss it with friends which furthers the unhelpful cognitive trap you’ve stepped into, leading you to the next negative experience perpetuating the discouraging cycle once again. I get it. I just ran through this entire process myself - but I noticed it, and course-corrected, which led me to a person I was SO excited about.

Dating is hard AF. It’s disappointing and frustrating, but it’s also a lot of other positive things. If you want to remain open to more positive dating experiences, CHALLENGE the narrative you’ve created. Start, pause, and identify your story about dating. Ask someone you trust like a friend to bring it to your attention when you’re doing it in conversations. You can’t challenge it, or change it until you’re aware of it.

Attempting to Minimize Pain

We all think if we ask all the right questions, have clarity about what we want, and meticulously choose people, we can perfect our experience, control the outcome, and prevent pain. WRONG! As much as I know this is impossible, I just went through it. I couldn’t believe I was “here” again; in pain and alone after how much I’d worked on myself, how much I’d grown, how differently I was choosing people, and how differently I’d been approaching dating. The person I was so excited to meet and be in a relationship with ended things abruptly and I was back in my own story of “you’re just not good enough to stay with”.

You’re not going to figure it all out. You can’t avoid painful emotions, nor should you want to because you learn more and more, the more you experience.  You grow from the negative ones, even if it feels horrible today. When you try to minimize pain and focus so much on your ideal outcome, you miss out on amazing people, learnings, and paths you might not have explored. People are also complicated, and you can’t control them, how they change, and how they feel. This pain, and navigating complex feelings and people, teaches you something important about yourself.

Casting a Wide Net

We often hear “it’s a numbers game” or that “love and emotions are abundant”. While I agree it is good to see who’s out there or get at it by “doing”, focusing on dating like it’s a cold sales process with infinite time and energy is hardly creating a rich, positive, or telling experience for anyone. Remember, you are a human being, and so are they. Scarcity will serve you far better. You can focus your attention on a person that’s interesting to you; “sitting” with them, and that experience to really know whether it’s right for you. You simply can’t do that when dividing your already minimal time and energy among many, work, kids, and any other parts of your life.

It’s also VERY easy to avoid real intimacy this way, which is so crucial at the beginning of a dating process. My single friends and I also commiserate often about how small the pool is out here in the Bay Area. But actually, when you reframe that narrative, the pool is small the more you know yourself, and know what you are willing and unwilling to compromise on, and that is not a bad thing at all! I have clarity about the qualities that are important to me, and what things are non-starters to me, so yes, there are fewer people as a result. Limit the number of matches, interactions, and dates you have in a short time frame. Give yourself the time and space to experience it, not rush through it. Pause, and repeat.

Trying to Wing It

Just like anything worth doing, dating takes significant time and attention. You simply cannot go with the flow and expect a high-quality dating experience. Regardless of whatever you’re seeking in dating from FWB to a long-term relationship, people seek available, thoughtful, action-oriented people. Make sure you have the headspace, and the time to dedicate to dating to make it a positive experience. Cramming dating into an already hectic life can make it feel stressful and overwhelming, whereas when you shift your priorities and intentionally date, it can be more fun, and so much more exciting! Honestly ask yourself what is happening in your life, and what time you have to give to dating, before you being.

There is nothing more attractive than a person with a plan. Be prepared. Be communicative and commit to dates, times, and activities. Interesting people want interested people! There isn’t anything accidental about someone who isn’t committing to a plan, or who “forgets” about a scheduled call or video chat. A “yeah I hope we can meet”, or “maybe next week” is communicating one of two things: they’re not that interested, or they have no intention of meeting you. So ask them for these things (and take note for the future), or move on.

Are you ready to make deeper, meaningful connections? Click the link below to setup your free discovery call to learn how I can help you navigate these tricky slopes!