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.