Horrible First Lines: How to Not Start an Online Conversation

When looking for love online, I’ve heard some of the most ridiculous attempts at opening communication. Sure, I do actively pursue a meaningful connection through internet-based means. But I am also realistic about the kinds of encounters I open myself to when using avenues such as dating apps. I’m realistic because I have experienced first hand the attempts some men make at initiating a conversation. Some crude, some rude. All unacceptable.

All of the following are real first-liners guys have used to open conversation with me.

The Insult


If you’re looking to start a conversation with me, do not start with insults. You are opening yourself up to a conversation for which you are completely unprepared.

The Pick-Up Line


The pick-up line is not always a swing and a miss. But, if you are going to commit to something so cheesy, at least bring your A-game. Would it kill you to spellcheck?

The Emoji


We all know what that emoji means… and this is the laziest way to go about it. Spoiler alert: second impression was also not impressive.



All things considered, saying hi in a gif is not the worst thing in the world. I would just appreciate slightly more effort. Maybe a question or a fun fact about yourself. “Hi” does nothing more than put the pressure on me to provide substance.

The Politics


I understand that having equal footing in political ideologies is important in a relationship. Just don’t start with tackling that beast. Ask me about my favorite color or if I enjoy the sunset more than the sunrise.

Besides, does he really even want to know my answer to that question?

The Try-Hard


Since neither of us had exchanged words, I do not see how I was playing “hard to get.” Needless to say, his attempt at a shortcut into the world of “outrageous flirting” did not go as successfully as he had hoped.

The Proposal


I mean… at least he knows?

Pro-tip: if your end game is legitimately finding a spouse, do not scare him/her off with an opening-line proposal. At the very least learn their last name!

The Desperation


Even back then, I could not pass up an opportunity to offer feedback. His approach was an exclamation of relief that does not translate well over text. I offered him plenty of advice, by the way. From opening lines to profile improvement plans. He got defensive and wrote off my feedback. I was just trying to help him find someone else to be interested (as I was no longer). Oh well!

Dating is hard. And striking up conversations with a total stranger could led to embarrassment and disappointment. It could also led to something great. So, here I am, trying to not give up hope in this muddled world of online dating. Until that day, my sassy side will pervade my online presence.

2 thoughts on “Horrible First Lines: How to Not Start an Online Conversation

  1. shatteredwishes

    What an awesome post! I have to say I have enjoyed reading your material and enjoying your work. Extemporaneous is officially on my list of favorite words to dumbfound the male population.

    You have a unique style, and are absolutely fearless, all while refusing to settle for the garbage that online dating has been throwing you. I hung up my OKCupid wings a long time ago, but that doesn’t mean I don’t understand what you are going through. And by the way, my screeename on my most chat/dating site is “Articulately Sexual” and boy do I have some tales regarding that one! (And yes, 99.9% of the male population just pretend they didn’t see the first word and just see the “Sexual”)

    Truth be told that was totally done on purpose, for that same reason. Not only am I just as fearless too, but extremely free and liberated in my sexuality. And the biggest guilty pleasure of all with having a screename like that? The absolute joy I get from saying to a “hi” message or a lame line like you have mentioned here in this post, by simply responding with. “What made you think you were worthy enough to approach me with bullshit like that?” *Snicker and win-win for women everywhere* ❤


    1. Lauren K. Ashler

      Thanks for the support! Dating is difficult. Online dating is almost worse. But I will keep trekking forward in my pursuits because I still have hopes that there are some good men out there. Until then, I’ll continue to post about those that aren’t so great!

      Liked by 1 person

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