Does It Feel Like Pulling Teeth When Having An Online Conversation?


In a world where we can hide behind our screens while we meet potential matches on dating sites, it’s important to continue striving toward authenticity. Self-discovery emerges as a guiding force in this journey, urging us to peel back our own layers and present ourselves in a light that goes beyond the superficial.

It all starts with crafting a thoughtful yet impactful response to others. 

Let’s face it, we are all getting a little tired of this type of online exchange:

“Hey, how are you?”
“Good, you?”
“I’m good.”

Psychology Today points out that when people feel they are lacking thoughtful conversations, it can cause a sense of dating fatigue. This is because they might feel like they’re not getting anywhere in their efforts to connect with someone.

We are here to help you turn this around! 

Explore how to transform mundane exchanges into meaningful conversations. Follow our strategies to elevate your responses and transition from online interactions to exciting first dates.

The Building Blocks of Curating Thoughtful Responses

Much like crafting a great dating profile, drafting a thoughtful message requires some intention that goes beyond a generic or superficial interaction. 

It’s about taking the time to consider the other person’s profile, demonstrating genuine interest, and responding in a way that fosters a meaningful conversation.

The building blocks of crafting a genuine and thoughtful response include: 

  • Personalization: Be specific when speaking to your match, mentioning a shared interest, complimenting something unique about them (non-physical is best), or asking about an experience they had. 
  • Engagement: Respond in a way that invites more conversation, such as sharing your thoughts, asking open-ended questions, or expressing curiosity about your experiences.
  • Expressing interest: Demonstrate that you are genuinely interested in getting to know someone through your responses to help move past superficial interactions.
  • Acknowledging shared experiences: Search for common grounds in their photos, bio, or prompts to help promote connection.
  • Respecting boundaries: Be mindful of other people’s level of comfort and avoid overly personal or intrusive questions. 
  • Maintaining a positive tone: No matter your level of interest in a match, it’s important to respond in a kind and respectful manner. 

Beyond this, it’s also imperative to consider smaller issues in your responses such as misspelled words or glaring grammatical errors. While dating platforms are a casual setting to chat and get to know other people, thoughtful responses require some attention to detail as they reflect a level of care and effort in the message. 

5 Practical Strategies for Thoughtful Responses

It’s incredibly empowering to showcase our real, unfiltered selves – especially while we are hidden away behind a screen. Not only does this help us connect with people who are most suitable for us in a deeper, more meaningful way, but it helps us let go of the uncertainty in the way we connect.

Here are some helpful tips to consider as you begin to match with potential suitors on dating apps: 

Embrace vulnerability 

One of the best ways to allow your authentic self to seep through the screen is by embracing vulnerability. Of course, this doesn’t mean exposing your deepest darkest secrets to a match you have only been talking to for an hour. Instead, it involves sharing aspects of yourself, such as your interests, values, and hobbies. 

For example, after noticing that your match loves to hike, you may want to open the conversation with a note about shared interest, saying:

I couldn’t help but notice we both share a love for hiking – it’s one of my absolute favorite ways to connect with nature and clear my mind (and get my dog out of the house). Do you have a go-to hike you like best in the area? I’m always on the lookout for new trails to explore.

Be honest with your intentions 

These days, it’s not uncommon for people to feel misled – especially in the context of online dating. When communicating with our matches, it’s important to express yourself in a way that aligns with your dating goals.

Are you seeking a serious relationship? Or are you looking for someone to date casually? 

Whatever your intentions are, it’s important to be honest. This can help build trust by ensuring you’re both on the same page.

Highlight your passions

Another helpful way to curate a thoughtful response is to highlight some things that bring a smile to your face. Sharing a tidbit about yourself such as your puppy’s name, your favorite way to spend a Sunday morning, or a particular experience that you loved can help drive conversation while also painting a more vibrant picture of yourself. 

This can also pave the way to discovering mutual interests and shared passions, fostering more meaningful connections. 

Avoid meticulously editing your responses 

Refrain from overthinking or spending time excessively perfecting your messages when communicating on dating apps. 

Sure, there are times when you may have to take a few minutes to come up with a great response. However, what is most important is that you incorporate your genuine thoughts and personality

The more you overthink, the less genuine you may appear – especially if the message reads as being more rehearsed or robotic. It’s more about embracing imperfections and letting the conversation flow naturally. 

Trust your instincts

When making decisions or judgments about potential matches and interactions, it’s always important to trust your gut. If you feel as though you’re forcing a conversation, there is no give and take, or you feel a little uneasy about a match (i.e. red flags are popping up early in your conversation), trust that your intuition is telling you something. 

Be kind and respectful when making decisions about whether you want to continue the conversation or not. 

The Bottom Line

In the world of online dating, where profiles can sometimes feel like curated glimpses, the authenticity, thoughtfulness, and intention we bring to our interactions can pave the path to a more fruitful dating experience. 

At Hidden Gem, we are here to improve your online dating game by helping you stand out against the crowd. 

Our Pearl Package offers expert dating guidance, suggestions, and answers to any dating questions you might have. This includes insight on how to start a conversation and keep it thriving. 

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