Lather. Rinse. Repeat.

The longer you date, the more you will notice that you keep getting asked the same questions over and over and over again. It doesn’t matter if it’s online during the messaging stage or in person when you meet. The same ones always seem to come up, and you can feel like a broken record on an endless loop, repeating yourself forever. It’s exhausting. At one point I was seriously considering starting up a document on my phone with the paragraphs all pre-written, so I could just copy and paste the answers in every time I was asked a question that felt like a rerun. I still might; sometimes I can be pretty lazy.

There’s a few important things to remember when you start to feel this way. First, if they are sending you questions then at least they are actually trying to get to know you. You could have just gotten a list of demands or a dick pick or an invitation to a hotel room or something. Second, you may have heard this question a hundred times, but they haven’t heard your answer at all. It’s old hat to you, but you are still new to them. Third, and possibly most important, consider this; if they ask you a question and you answer it, you get to ask it back with the reasonable expectation of a response. It might start an actual conversation. If you have been online dating for long you know how hard that can be.

If you are also considering setting up a few prepared answers, want a little preview into what you will inevitably be asked eventually, or need ideas for starting a conversation, here are the most asked questions I’ve received while online dating.

“How are you?” Generic. Boring. Uninspired. But at the same time, it is how most conversations with people you already know start, so it’s not entirely unfair. It even has the potential to show genuine care or concern. It most likely doesn’t, but the possibility is there at least. The biggest issue with this question is that in most cases you are going to get too short of an answer or too long of one. It’s not technically a closed question, but it is very easy to answer with just one word. Good. Fine. OK. Or if it goes the other way you might wind up with a 3-page diatribe about how they are feeling about something that happened at work or with an ex. Valuable information maybe, but not something you need right now.

“What’s up?” Or it’s backwoods cousin “Sup?” Similar to “How are you?”, this is a very common message, and a very lazy one. Let’s face it; if you were currently up to anything really interesting you wouldn’t be online answering your messages. Yet somehow something that used to be an actual exploratory question about why someone was contacting you has turned into an introduction designed to force the recipient to say something that entertains the sender.  

“What do you do for fun?” Depending on your dating platform this question is either good or lazy. If you are on something like Tinder that doesn’t allow you much space to write a profile then it is good, the person messaging you is trying to find out what you like, if you have any compatible interests, what kind of free time you have, etc. However, if you are on a site like Plenty of Fish and have completed your profile then this information should already be out there for them to see. By messaging you and asking you something they could see with just one mouse click they are telling you that they aren’t interested enough to do even that.

“What are you looking for?” This is a great question, if you know the answer. If you don’t, well, you are probably going to fumble a few times trying to give one. In general, it’s a good idea to know what you want before you go looking for it, but when it comes to dating, most people don’t. Answering this a few dozen times might actually help you figure that out.  

“Why are you single?” In my opinion this question is a little mean, even when asked in the most flattering way. First, it is very difficult to answer with any kind of positive spin. ‘I’m picky’, ‘I haven’t found what I’m looking for’, and ‘I am only recently single’ all have negative connotations that go along with them. And those are the easy answers. Second, a person who has been online dating for a while is probably already asking themselves that question. The realization that finding someone online isn’t fast or easy hits us all differently, but having someone else point out to you that you haven’t found someone yet and that they can’t see why is hard for anyone to hear. Particularly if they wind up being yet another person that isn’t for you.

Messaging

You’ve come up with a great screen name, taken some awesome pictures, and done a funny write up. Your profile is finished and you have just hit the button putting it out there for the world to see. So what’s next?

Welcome to what I like to call the feeding frenzy. Depending on the size of your market, your gender, and your orientation you are about to be hit with a few weeks of seemingly endless messages and offers, likely more than you ever expected. Think of it like sharks in a pool, and your shiny new profile is chum in the water. Every hungry predator out there is going to come over, have a sniff, and see if they can get a piece of the fresh meat. All you can do during this time is hold on tight and wait for the maelstrom to end. It will be overwhelming, I promise. 

If you get past this period of insanity without becoming insane yourself you will be ready for actual online dating. You know, the part where you actually have to do some of the work. I can almost hear you saying “But wait, didn’t I do that already? Isn’t that what my profile is all about?”. Nope, not at all. Think about it like an advertising campaign; your profile is the billboard, but you still need to do the work to get people to want to buy your product. When it comes to online dating your best tool to attract foot traffic is messaging. 

There are a lot of people who online date that do not understand how to communicate. I’m not talking about people who can’t figure out how to type, don’t know how to form a sentence, or don’t understand that the pinging sound from their phone means someone is trying to get in touch with them. Those people are lost causes and will weed themselves out pretty quickly. I’m talking about the people who don’t understand the basic rules that should be followed when communicating with a human being for the first time. Here are a few of them to get you started.

Spelling and punctuation matter. Remember those grammar classes in elementary school? The ones where you learned how to capitalize the first word in a sentence, and how to put a period at the end? This is where that comes in really handy. The very little bit of effort it takes to use whole words and form fully structured sentences will pay off tenfold, I promise. This is your first real interaction with someone you are interested in; do you want them to think you are too lazy to type all nine of the letters in ‘how are you’? Probably not.

Don’t be negative. This one is huge. There are very few things that turn people off as much as someone who is whiny, makes irritating assumptions or unfounded accusations, and is so self-deprecating you wonder how they even get out of bed in the morning. Try and remember that you are trying to find someone to date here, not just looking for free therapy online. Sure, it’s good to be able to talk about anything and everything, but if you are only ever talking about your ex, your health issues, your problems at work, or whatever else has you down you are not going to come across as very attractive. Negativity is a giant buzz kill, and as soon as you go there the person you are interested in will lose interest in you. 

Ask questions. I know, it seems simple, right? You are trying to get to know someone, and the easiest way to do this is to ask them things. You would be amazed and how many people can’t figure this one out. They will answer asked questions, but won’t initiate any of their own. I also recommend asking open ended questions, the kind that can’t be answered with a one-word answer. How thoroughly they answer questions can tell you a lot about a person, and about how willing they are to let you get to know them.

Non answers. I don’t mean not answering, we will get to that in a minute. What I’m talking about here are those answers that are non-specific fluff, the ones that are so generic and non-committal that it is impossible to respond to them. Good, fine, lol, OK, and other words like that. Ones that make responding really difficult for the person you are talking to. Think of a conversation like tossing a ball back and forth; asking a question is throwing the ball, answering a question is catching it, then opening up a new topic is throwing the ball back. If you miss that last step and you let the ball drop it is very likely that the conversation will go with it.  

Tone. SARCASM DOESN’T TRANSLATE VIA MESSAGING. I’m sorry, but it’s true. No one has come up with a sarcasm font yet, and a new person reading your words for the first time is not going to know that you usually have your friends ROTFL with your acerbic dry wit. They are just going to think you are mean, confused, or stupid. Save your sarcasm for when they know you a little better; I’m sure it will be a super pleasant surprise for them later on.

Be original with your introduction. Let’s face it, there are a lot of people online dating who do not fit anyone’s standard definition of attractive. Not by far. This means that anyone who does fit into that definition, even just a little bit, is getting a lot of messages. The feeding frenzy may have never ended for them. They are probably constantly bombarded with an endless stream of “Hi”, “Hey”, “Sup”, “How r u”, “DTF”, “What’s up”, and other greetings that are just unbaited hooks thrown in the water to see if anyone will bite. Bait your hook. If you haven’t received a message from them they either aren’t looking at profiles, or yours wasn’t enough to get their attention. Your first message is your next opportunity to do that. Look at their profile, find something that you know things about in it, and send them a question about it that will make them realize you have more in common than the app you are using.

Time between responses. How long you take to respond to someone, and how long they take to respond to you, is a big indicator of how interested you are. It’s a very simple formula; quick and timely response = interested, increasingly longer periods between response time = losing interest. You can make all the excuses you want (work, kids, friends, etc.) but what it ultimately comes down to is that people make time for things that interest them. If someone isn’t making time for you then it’s time for you to move on.