The “How Was Your Day?” Conversation in Online Dating

Finding Meaningful Connections Beyond Simple Questions

DateSmart40
Dating Advice from DateSmart40
5 min readJul 28, 2024

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A couple in their 40s texting on their smartphones, both smiling and engaged in a lively conversation, in a cozy living room setting,
(AUTHOR DALL E3)

Online dating often begins with simple questions, but meaningful connections require more depth. This discussion from daters over forty reveals the challenges and strategies for moving past repetitive conversations.

The OP — Props_Abridge_1978, frustrated with repetitive questions, seeks advice on how to communicate their need for more stimulating conversation. Here’s what they wrote:

“Is anyone frustrated with non-stimulating conversation when getting to know someone through OLD? I would like to get off this ride. Specifically the daily loop of the same (boring) questions: How was your day? How was your sleep? Some chatter about the weather. Yes, those are intro questions.

But the conversation should go somewhere after being asked how your day was. Surely there are other things to talk about. I’ve met up with a guy a couple of times. Already having mixed feelings about intellectual and physical attraction. Now I’m not feeling the effort when I get the daily “How was your day?” How to let him know politely I don’t find the conversation stimulating and think we should leave things?”

Seeing “How Was Your Day?” as an Opportunity

Many daters advised that the question “How was your day?” can be an opportunity to steer the conversation.

Responding with Details Several contributors suggested using detailed responses to make the conversation more engaging.

“The guy I have just started dating texted ‘how was your day?’ I had an initial feeling of ‘ugh, really?’ then I realized it was just his attempt to reach out and connect. So I told him how my day was with a little anecdote and we chatted about that for a bit, then I volleyed it back with ‘how was yours?’ and he took it from there, talking about something he did and we talked about that.” — Full_Tilt shared.

Black_Swan67 emphasized giving the other person something to work with:

“You have to give them something to go on. If someone asked today ‘how is your day going?’ I’d probably say ‘Not too bad. It’s my last day in the office so I’m working from home tomorrow which is always nice. I’m going to Pilates after work so I’m looking forward to that. Right now I’m slacking off a bit reading about how the Southwest change to their seating. Can you believe that?’”

These responses highlight that an initial generic question can lead to deeper conversation if met with interesting details.

Turning Boring into Engaging Some daters highlighted how to transform mundane questions into engaging dialogue.

“It’s an opening to start a conversation but it also provides them tidbits about what your daily life is like. I do get annoyed when I get into detail about my day and then they say ‘fine/okay/great’ when the question is volleyed to them. It isn’t a boring question unless you make it into one.” — Cake_Lover pointed out.

Balancing the Effort in Conversations

While many saw potential in the simple questions, others felt it should not always fall on one person to carry the conversation.

Equal Participation SobtoBlobs stressed the importance of both parties contributing to keep the conversation lively:

“I agree with this but there is also a point where if I’m doing alllllll that extra conversation work 100% of the time then it’s not a match for me.”

SetToSwing added:

“It’s a conversation opener that leads to other topics and demonstrates interest. I can tell you there are many men online that could care less. I think you are overthinking this. Create the stimulating conversation you want to see in the world.”

These quotes emphasize that while opening questions might be simple, both individuals need to make an effort to keep the dialogue engaging.

Identifying Compatibility Several contributors mentioned that repetitive and unengaging conversations might indicate a lack of compatibility.

“Then that’s the sign they aren’t the person for you!” — PositiveSeason1970 succinctly put it.

LeanneS44 echoed this sentiment:

“This leads me to believe you have nothing in common with this person if it’s an ongoing issue. Best to keep it moving if you simply aren’t interesting to one another and it feels like pulling teeth.”

Meeting in Person

Some daters suggested that in-person meetings might reveal a different side of a person that texting cannot.

Seeing Beyond Texting EyeonSpace shared their preference for meeting in person to truly gauge compatibility:

“If you feel that you can have an initial conversation with someone my preference as far as possible would be to at least have an initial meeting. Myself and some people I know are bad at texting, but figuratively the ‘life of the party’ when you meet them in person.”

This advice suggests that text conversations might not always accurately reflect a person’s potential for stimulating conversation.

Takeaway

Moving beyond the “How was your day?” question in online dating can lead to more meaningful connections. Here’s what we’re taking away:

  • Respond Creatively: Use the opportunity to provide detailed and interesting responses.
  • Equal Effort: Ensure both parties contribute to keep the conversation engaging.
  • Identify Compatibility: Recognize if repetitive conversation points to a lack of connection.
  • Consider In-Person Meetings: Sometimes, in-person interactions reveal a different dynamic.

Tips to Start the Conversation

Here are three ways to open the dialogue with your partner:

  • Share an Anecdote: “Today was interesting, I tried something new and it made me think of… How about you?”
  • Express Genuine Curiosity: “I’m curious, what’s something that made you laugh today?”
  • Suggest a Meeting: “This conversation is fun, let’s continue it over coffee sometime?”

Happy Dating!

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