Playful Empowerment LLC

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Taking The Lead In Conversation

Hi, I’m Amanda. Welcome to my blog, where I share online dating advice, tips, tricks, and strategies, all based on my professional training and personal experience.

What comes up for you when you think about making the first move in online dating? About being the first to initiate contact, rather than waiting to see if that person reaches out to you? If you’re like other women I’ve talked to, you might look at me like I suddenly have five heads, outwardly cringe, or want to crawl under a rock somewhere. Initiating conversation on dating apps can be incredibly daunting and scary for women for a whole host of reasons.

Grab my free Online Dating Red Flags Checklist, so that you know what to look for in matches, conversations, and dates.

First, it’s vulnerable. It opens us up to rejection and uncertainty when we send a message. You don’t know what you’re going to get back: a cruel response; a rejection, which even when done tactfully, is still a rejection; or radio silence, which can sometimes feel worse than anything else. When you hear nothing, your brain doesn’t get closure, potentially creating an endless loop of different scenarios and possibilities for you to ruminate on. In contrast, if you wait for other people to message you, it decreases your sense of vulnerability, knowing that the person is already interested. There’s safety and security in knowing that a person has already vetted you and was interested enough to take the lead themselves.

Second, there’s the question of how to do this. What do you say that doesn’t sound cliche? How do you open up a conversation that doesn’t feel forced or disingenuous? You don’t want to be the person who just says “Hey”, since you know how infuriating that is. It feels easier to wait for other people to message you, rather than try to start up a conversation that feels forced or fake.

The downside of taking this approach is that you only see a segment of the potential match pool. It’s kind of like trying to figure out what your favorite flavor of ice cream is when you’ve only sampled vanilla, chocolate, and strawberry. You might not necessarily dislike those flavors, but that gives you a very limited palette, compared to trying the 98 flavors (and growing) of Ben and Jerry’s. It can feel easier and more comfortable to stick with the vanilla, chocolate, and strawberry, but in doing this, you may not even realize that other flavors (my favorite: Pumpkin Cheesecake) actually exist.

There is a different way of approaching conversation as women, which is focusing on who YOU want to initiate conversation with, rather than who is messaging you.

Only focusing on the people who message you can be a huge waste of time and energy. Think for a minute about the spam folder in your email. How often do you actually go through your spam messages? Probably not very often. You likely select “delete all” every now and then, knowing that there’s nothing worthwhile in there. Or you might skim from time to time to make sure you didn’t miss something legit. But most people don’t open each email, go through the content of each one, and become outraged by how horrible each spam email is. And yet this is what many of us do when it comes to online dating messages. (Yes, I was guilty of this as well.)

Feelings of guilt and obligation can also be a result of this approach. Imagine receiving a “good” message from someone, and yet knowing in your heart that you’re just not interested. Are you able to just click delete? Or do you feel obligated to respond and send a polite rejection? Maybe you want to provide closure for the other person, empathizing with how awful it feels to sit with the ambiguity of unanswered messages. While that’s a very compassionate thing on one hand, it also means that you’re spending a lot of your mental space on people you know aren’t going to be a fit for you. This builds further negative associations with online dating and reinforces the idea that there’s no one else out there.

Yes, it is vulnerable to take the lead and initiate conversation. Yes, it’s scary to open yourself up to the unknown. But it’s also empowering, because you are focusing on YOU. Your thoughts, your feelings, your gut reactions, who YOU like. This might not sound like a huge shift, but mentally and emotionally it is. Your choices and decisions are fully back in your hands, rather than being swayed by the fact that someone showed interest in you. Your focus is on the matches that make you light up and give you the butterflies feeling. That gets to be your starting point. It’s like spending time crafting emails to people you actively want in your inbox, and saying goodbye to spending time in your spam folder.

So with how scary this can feel, how do you get comfortable taking the lead?

It’s important to remember that vulnerability goes hand in hand with empowerment. If you’re not already acquainted with Brene Brown’s books, podcast, TED talks, Netflix special, etc., this might be a good time to do so. She does a great job of reminding us that we can’t have love, joy, meaning, and success without also having failure, hurt, rejection, and heartache. The two go hand in hand. It’s ultimately about choosing the life that you want to live. You can take the safe route, but it’s going to be less rich and expansive. Taking the hard route is difficult, but it also means opening yourself up to all of the amazing aspects of life that all of us crave. Brene’s quotes are posted on my fridge as a reminder that the excruciating parts of life are necessary to have the absolute best parts of life.

Rejection hurts, but it’s also important to remember that relationships are about fit. It’s all too easy when we’re rejected to fall into a mindset of self-blame. We question what’s wrong or not good enough about us, and yet this mindset isn’t helpful, nor is it accurate. Relationships are about fit. A lot has to line up in a connection or relationship for it to work. If someone is rejecting you, you weren’t a fit for them, and that’s okay. When we’re in the moment, and experiencing the pain of feeling alone and rejected, this can be hard to recognize. However, think back to some of your past crushes or relationships, and think about where those individuals are now. Would those connections have ever worked? I know that it certainly wouldn’t have worked with a college crush of mine who now has four children, whereas I’m childfree by choice. It makes sense now, but at the time, all I could think was, “Why am I not good enough?”

Uncertainty is also challenging to deal with. With online dating, there are going to be numerous times where you’re not going to get the answers that you want. However, because our brains naturally want certainty and predictability, we can convince ourselves that we’re the problem, that we said or did something that led the other person to not respond. In reality, they may have just hit their limit with dating and decided to stop responding to messages. Or maybe they had life circumstances that took them away from dating. Regardless, we may never know. The solution here is to acknowledge what you don’t know. Redirect your brain away from its attempts at problem-solving and instead sit with the phrase “I don’t have the answer to this question.” Easier said than done, I know, but with practice, it becomes easier.

If you’re struggling to come up with what to say in a first message, think about what drew you to the person's profile in the first place. Was it a funny comment they made? Was it a similar interest? Do you share a hobby? Start with that. Start with the natural connection points. And consider that if you’re really struggling to find a connection point, it could be a sign that the fit isn’t there. Also, generic questions are okay, and can still give you data. Let’s say you send a message that says, “Hey John, how was your weekend?” He replies, “It was great, I spent time with my family and went to church.” Are you a person who is religious, or are you atheist? Do you also spend every weekend with your family, or do you talk to your parents twice a year? A simple question about the weekend just gave you a lot of information to go on.

So next time you’re on the apps, ask yourself: Are you ready to take the lead in your online dating journey?

*Don’t forget to grab my free Red Flags Checklist! You’ll learn everything you need to know to scan for red flags in your swiping, conversations, and dates.