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.

Disappointment and Disgust: an almost mistake

I wish I could say I was not cynical. I wish I could say I trusted easily. But, life experience hasn’t quite led me down the road of a Disney-princess naivete’.

Let me back up approxiately a week. I was swiping on Tinder and came across an interesting profile. Despite my lack of interest in dating a teacher (I myself am in the world of education and have found the whole thing unappealing), I swiped right on a man whose profile says he is a high school history teacher. We matched. I kept swiping.

His opening line was a sad attempt at a joke. I responded with my usual brand of sass and the conversation progressed. Come to find out, he left education for reasons I’m sure most educators in the current climate would understand. Okay, so not a teacher. I can totally handle that. Then I find out he is also a member of the National Guard…

It truly is difficult to explain how much this realization was humorous to me. No matter how much I avoid active duty soldiers, they seem to find me. I have nothing against them. I have dated quite a few. But never do I seek out a man in uniform. It just happens to be the most common theme of man the universe keeps throwing my way. Obviously since I am still single, those men haven’t worked out in my favor; but, I digress…

Consistent messaging for nearly a week had me wondering why he didn’t ask for my phone number. I am neither shy nor subtle, so I pointed that out quite clearly. I must’ve stolen his thunder but he relented and asked for my number. Some quick messages were exchanged before exhaustion caught up to me.

The next morning, I decided to use my newfound information (his number) to do a bit of my own private research. Sounds sort of creepy, I suppose. I have just found that knowing a bit about a person through their online presence helps me gauge compatibility. Plus, meeting strangers is a dicey proposal. I’ve found it best to arm myself with the most information. Safety in knowledge.

His profile popped up on Facebook after a quick search of his phone number. It didn’t take long to ascertain from comments and photos that he is, in fact, married. Now, those who know me know I have zero respect or tolerance for infidelity. Vehemently so. That choice has never been one I’ve been capable of understanding. So, I’m glad I found this out sooner rather than later. Saved me some trouble and heartbreak. On to the next.

But he messaged me. How could I resist?


This was it. This was the moment he would set out to convince me the marriage was over. He was unhappy. She had left him. They were getting a divorce. They were separated. This had to be the moment.

It was not that moment.


His response made me even more upset than if he had tried to return to my good graces. It was cavalier and flippant. How could anyone be so casual about this?

I struggle with the idea of sharing this information with his wife. I’ve taken screen shots of his profile and our conversations. I could easily reach out. But, as difficult as it is, I don’t really think it’s my place to get involved in their marriage. He does not seem particularly intelligent or like he is going out of his way to hide it. She will find out eventually. I will not be the person to get in the middle of a relationship, let alone a marriage. And how dare he put me in that position in the first place.

Simply walking away was not an option though. Not for this sass-and-opinion-filled lady.


K. Bye.


Online Interactions

I like to ask people when first getting to know them the following question:

If you had to describe yourself using only one word, what would it be?

You’d be surprised how boring some of the responses can be. Many men like to say “driven.” And while that is absolutely a good quality, I think it says little about the man I’m trying to get to know. I am not interested in a man that isn’t driven. Been there, done that.

I would never ask someone a question I wasn’t willing to answer myself. This is sage advice from my mentor at work. Reciprocal self-disclosure, if you will. My word? Sassy. Over the course of my encounters with online romance, my sassiness has been unleashed, typed, sent and thoroughly documented. Screen shots for days.

“come cuddle”…Opening line courtesy of Patrick from Tinder.

Call me old fashioned, but even though I have searched for love in the vast expanse of the internet, I am still looking for a meaningful connection. In fact, one of my best relationships started with swiping right (a story for a different post). Sure, perhaps I am naive to think that men should try to get to know me before asking me into their bed. But that’s just the kind of girl I am. So yes, my sass comes out in full force if they open that door.

While not all of my conversations are sass-laden, I have captured the hilarity and shared with my friends the countless conversations that are beneath the efforts of a Mr. Darcy. But many are just too good to keep to myself. So, I present you with my online interactions…