While we are on the subject of online dating, I have a few more things to say. We spent so much time talking about the dos and don’ts of profile pictures last time, I feel like I’d be remiss if I didn’t address the subject of online dating communications. What to say to that potential someone. And more importantly, what to never say. So much of what I’m about to cover seems like basic common sense and good manners. But clearly, it needs to be said because there people are out there, on the World Wide Web, saying some terribly stupid things.

I gave the internet singles scene a try, for the very first time ever, last year during the holidays. Why I thought bringing an added layer of shame, disappointment, and violated expectations to my holiday season would be a good idea is beyond me. But never the less, I decided it was as good a time as any to throw myself to the wolves and whittle away at what romantic hopes I have left.

I did zero research before deciding which sites to try. I joined Plenty of (Old, Creepy) Fish and Tinder. Yeah, I know. Perhaps not the best ones to start with. But here’s the thing. Actually, two things. Thing one: I am a big believer in the idea that you get what you pay for. I get the theory that if you sign up for one of the sites that you have to pay for, you will encounter men (and women) of a higher quality. But to that I say eh, maybe. But maybe not. And now you’re not just disappointed and wondering if you really will die alone, you are also out $19.99 a month. Or whatever it costs, I didn’t look that far into it. They lost me at “Enter your Credit Card Info Here”. Thing two: Color me naïve and clearly I was late to the party, but I really didn’t know that Tinder is less about finding someone to date and more about finding someone, anyone within arm’s reach, to have an adult sleep over with.

So, Plenty of Fish. It started off great. My profile wasn’t even complete before I had five messages in my inbox. And anyone who has ever tried online dating is intimately familiar with the quickness with which you can go from thinking “Oh, this is going to be awesome. I’m the most popular person on the internet and I just got here!” to “Wait, what? OH, my God. Who says that? Where am I? What is happening?”

I will be the first, THE FIRST to say that initiating a conversation online is the worst. It’s so hard. There is nothing natural about it. You can ask all of the thoughtful, profile-relevant questions you want. It all sounds like contrived bullshit. That goes for me, as well. Oh, all of the things I say in these online conversations is complete garbage. No matter how hard I try to sound witty and interesting, it’s just awkward awfulness. So with that being said, I do what I can to stay open minded and not be too, too judgey when I receive messages.

No, I’m a liar. I try to not to judge you so long as I think you A) made an attempt to get to know anything about me via my profile B) write an original message, not just copy and paste the message you send to all the girls, and C) at least try use English grammar correctly.

Excuse my French here, but what the fuck? I know I spent an obscene amount of my 20s and 30s in monogamous relationships and as a result, I have done very little “dating”. But no, seriously. What is happening to the way men and women are communicating with each other? And when I say “the way we communicate”, I am not referring to texting, emails, or online dating messages. I mean the ridiculous shit people are saying to each other (read: dudes are saying to me). Subtlety seems to be a lost art. Let’s take for example a couple of exchanges I had with a gentleman I bumped into on Tinder. Again, I remind you, I didn’t know that it was mainly for hookups. Though now, in retrospective, it all makes a little bit more sense.

So, this here was our first exchange. I pick it up about three exchanges in. Don’t worry. The beginning of this conversation was just as tedious as what you’ll see below.

Now, I will side step his boring and generic line of questioning as well as his use of the word “yummy” and the fact that he said he’s staying away from carbs for a few days. Fast forward through some more boring questions and answers, he gives me his phone number, and we move this stimulating conversation over to text.

No, really. That happened. We were talking about the fact that he made his headboard, to which I said, “That’s awesome”. Do you see how, without so much as an attempt at a transition, he went right into telling me what a bad boy he was? AND do you see how a man in his 40’s referred to himself as a “bad boy”? I can’t.

But wait. There’s more.

Right. So again, he goes from discussing something as normal (and uninteresting) as decorating Christmas trees to asking me about MY BODY with no work up at all. AT ALL. It was right about here that I told him “Thanks but no thanks” and blocked his number (my signature move).

Side note: To those asking why I would continue to entertain a person who was boring me so, I have two answers. When you are a woman of a certain age and single, people are always telling you to be open minded and give people a chance. So that was what I was trying to do; give him a chance to say something, anything of substance. Also, pickings are slim. It was an attempt to work with what was available. Lesson learned.

Recently, I received this gem. While I am sure the intent was to be complimentary, it was not received as such.

Oh, shocker. Me and this guy are a 0% match. Ok, the fact that he has capitalized not a single letter in his message makes me sad about the future of America. And when did I become the older woman that a dude in his 20s is interested in “experiencing”? Fuck my life. The best part? Joke’s on this dude. He may have stood a chance if he didn’t refer to me as an older woman and if he sounded remotely intelligent. Everyone knows I like ‘em young.

Look, I’m not pretending to have the answers on what TO say or how to initiate (or carry on) an online conversation with any level of quality. I’ll be first to admit it, I have no idea what I am doing. Because as I learn over and over again in my old age, I have no game.

In fact, if anyone wants to give me some good pickup lines to use in online forums, I’m all ears.