Dear Dr. NerdLove,

I'm a sociable person who enjoys meeting new people and sharing experiences. I've had a rather unique life in my twenties, and friends often describe me as friendly and at ease. I thrive on learning new things and forming friendships when I'm out and about.

However, online dating throws me for a loop. I struggle to initiate conversations and would much prefer face-to-face interactions. I understand the hesitations women may have about meeting in public, yet I feel uncomfortable asking someone out in those settings. Consequently, I find myself on Tinder, matching with people, and then faltering with a timid "Hey." In contrast, I have no qualms about chatting with strangers on a Friday night about which bird they'd embody based on their personality.

It would be fantastic to navigate this better, as I'm keen on building a deeper connection with someone.

Thanks for your help!

Just Say The Words

Let's address an aspect of your letter that may not seem directly related but likely ties into your difficulties with initiating conversations on Tinder.

You express concern that asking someone out in person feels like navigating an ethical quagmire. This suggests a fear of rejection that has morphed into a worry about potential consequences. Many people hesitate to approach someone in a bar, club, or public space because they fear making the other person uncomfortable or coming off as creepy. However, when we delve deeper, the real concern often revolves around the fear of becoming the "Main Character" in a negative social media story.

While those worries aren't unfounded, they often exaggerate the likelihood of a severe backlash or shame. Yes, risks exist, but so do the chances of being struck by lightning or facing other unlikely misfortunes.

Typically, the behaviors criticized in dating contexts involve guys being rude or ignoring clear disinterest from others, not those who engage in pleasant conversation before asking for a date or phone number.

If you're socially adept enough to sense when it's appropriate to flirt, and your invitation is casual—like grabbing a drink or visiting a museum—then the chances of offending someone are quite low. If you can gracefully accept a "no" response, you're on solid ground.

Now, back to your question.

It's intriguing that you find starting conversations on dating apps more challenging than in person. Many individuals find online interactions less intimidating since texting allows for more contemplation before responding.

The key point here is that you must actually initiate the conversation. Whether you're chatting on Tinder or standing next to someone at a bar, your goal remains the same: to get the conversation rolling, something you're already skilled at doing in person.

And here's the reality about dating apps: the expectations are surprisingly low. Many men send messages averaging just a few characters—often "hey" or "what's up." This brevity frustrates women, making it tough to engage meaningfully. By offering something to respond to, you not only stand out but also make it easier for the other person to engage.

Moreover, if someone has a well-crafted profile, there are ample conversation starters. Do they mention favorite foods or books? Use that as a jumping-off point. If their profile is sparse, you can still draw insights from their photos, asking about experiences or moments captured in those images—avoiding comments about their appearance.

Remember, you don't need to be flawless, witty, or the smoothest conversationalist. It's not about outsmarting or outshining others; it's about being engaging and enjoyable to talk to. Women on dating apps face similar challenges in starting conversations and can feel just as anxious. Making it easier for them to engage with you enhances the experience for both parties.

An effective strategy is to ask questions. Questions invite dialogue, especially those related to their interests. This approach increases the likelihood that they will want to engage with you instead of someone else who may lack depth. Just be careful not to dominate the discussion. Show genuine interest in their thoughts, and let them guide the conversation.

A useful technique is to request a recommendation. For instance, "Hey, do you like [Author]? I'm curious about starting with one of their books. Which one would you suggest?" This not only engages them but also positions you as someone who values their opinion.

Good luck!

Dear Dr. NerdLove,

To sum it up, I had a crush on a coworker who was recently let go. I found her on Facebook and messaged her. My initial greeting was simply, "Hi, [Name]," to which she responded. Later, I checked in with, "Just wanted to see if you're okay," and she replied with a heart emoji. I then tried to deepen our conversation by asking, "What do you like to do for fun?" and added, "Because I hate the thought of not seeing you at work anymore." Unfortunately, she didn't respond.

First, I’d like to know what was wrong with my message since some friends said it came off as creepy. Second, I really like her and hope to salvage this situation. Is there a way to do that?

– Was It Something I Said

Oof.

You weren’t creepy, but you didn’t exactly shine either.

Let’s start with the reality that there’s likely no way to recover from this. Not because you made an unforgivable mistake, but because there wasn’t a genuine connection to begin with. Attempting to build something from a lack of foundation is challenging.

Your approach may have inadvertently put her on guard. While finding her on Facebook isn’t inherently wrong, it raises concerns if there's no existing friendship. Plus, if you're not connected on social media, your messages may not reach her right away.

You reached out during what was likely a tough time for her. Getting fired is difficult, and most people feel low afterward. If you don’t have an established connection, it might come across as opportunistic to flirt.

Initially, you were on the right track by checking in on her after her job loss. It’s thoughtful to show concern, even if you aren’t close. A kind gesture can make someone feel cared for during a rough time.

However, your next message shifted the tone. Asking about her hobbies felt out of place right after expressing sympathy. It suggested that your interest in her was more important than her current situation.

Following that, your comment about missing her at work was presumptive and self-centered. It conveyed a lack of emotional awareness, making her situation about your feelings instead of hers.

It's crucial to recognize when the right time for certain conversations is. If you had established a friendship, expressing that you would miss her presence at work could have been acceptable. But given the context, it felt inappropriate.

What can you do now? Let it go. There’s little chance of rebuilding this connection, and you should focus on learning from this experience. You had a moment to show empathy, and had you stopped there, you might have had a better chance of developing a friendship.

The lessons here are:

1. Build connections before significant changes in someone's life occur.
2. When reaching out to someone you don't know well, keep it brief and respectful.
3. Avoid making advances during someone else's difficult times.
4. Don’t assume familiarity that doesn’t exist.
5. Prioritize sensitivity over your feelings in such situations.

Now you’re aware. Learn from this and strive to avoid similar pitfalls in the future.

Good luck.