Congratulations! Someone has responded to one of the four hundred online entreaties you sent to people who’ve caught your interest on an online dating site. It is not easy to write to 40 or 50 strangers every week and the rate of rejection can be very discouraging.

Since even a 5 percent return rate on those messages is, by itself, an accomplishment, take a moment to pat yourself on the back. The rejections are not all about you. The companies that run dating sites have very little incentive to reduce the appearance of large populations. People are testing the waters, people post profiles to see how many responses they can get so they can feel good about themselves, people get fatigued and leave profiles up months after they stop checking them, and some people are just unpleasant.

If you’re getting a worse response rate than one in ten or one in twenty though, it is time to refresh your profile, check your wardrobe, get better pictures, and retrench.

However, having gotten a real response, you now face a dilemma: how much communication should I have with this person? And what are the rules of texting before a first date? 

The first step is to establish a degree of rapport

Hopefully, the short paragraph you wrote to the person in whom you’re interested contained some questions and they’ve been answered. The answers should give you something to riff off of; if your initial message asked what tracks had been getting a lot of play on their headphones lately, then the next question might be whether they’ve ever seen that artist in concert.

You’ll find that if you include a question in every communication that people will naturally tend to answer them. Conversely, if you do not ask a question, when you’re getting started, you will see that the exchanges tend to drop off and will wither away. Note also that it looks bad when you forget to close with a question and then you attempt to correct by asking one; get into the habit of never clicking send without a question in the response.

There is no shame in going back to carefully read the person’s profile another time. If you need things to ask questions about, then by all means, go and do some review. Unless they invite the divergence, then keep the subject matter light. Even if you met on a dating site for leftist militant vegans, keep it light and ask about different things from their profile. It is easy to drive a conversation down a dead end street and changing the subject will be awkward if not outright jarring. If you find yourself running out of things to say, you have probably overshot the time for an in-person meeting.

Some things to consider before you try unprotected text

So your dream mate, or more realistically someone who could be your dream mate if you got to know them, has been promptly answering your questions, asking questions of their own, and you’ve got something going. They appear to be human and can manage to not appear scripted. Great! However, be careful.

A secondary reason to ask questions is because a script-bot is not really capable of even the most basic of Turing tests. If you ask about the music someone has been listening to lately and they respond with “i’m looking for my soulmate, do you have snapchat?” then you’re probably interacting with a bot. Even if the bot is somewhat sophisticated and can parse your messages for keywords, i.e., “music,” and offer a canned response, they will run out of responses in a hurry and attempt to move the conversation to text, or another messaging program. Report and block them; while it can be momentarily entertaining to start asking the bot absurd questions and giving ridiculous answers, ultimately it is just a simplistic set of “if-then” routines and you’re wasting time.

Consider very carefully whether or not to terminate things instantly if someone requests that you move from dating site messaging to another online messaging service. This request makes no sense, you just replace one app with another. The only thing this does is move you out of the, somewhat, sheltered environment of the dating site, to someplace with fewer protections. If there are good reasons for this request they remain a mystery.

If someone offers you their cellphone number to text with, and does so after a dozen or so messages over the online dating site, then it is usually fine to move the conversation there. You, however, should never be the first to offer your phone number; it looks overly eager and suggests you’re the one who is more interested.

Appear as interested as they are, do not be more interested. The sole exception here is that if you have not exchanged numbers by the time you are set to meet, send a message with your cell and say that it is so they can reach you if anything goes wrong. Of course, since all of the dating sites have phone applications, this is not actually necessary but by offering up your number in this way you look thoughtful instead of needy, and of course now they have your number.

As another aside: if they offer you an unfamiliar area code, then make sure it fits in with what you know about them. If your prospect says “I just moved here from Nevada” and then a couple days later sends you a Vegas area code, then you can lower your defenses somewhat; lowering them all of the way is unwise and requires an assessment, by you, of how credible the moving story sounds. We all know people who just never changed their cell numbers after moving and, since almost no one actually dials numbers anymore, this is a yellow, but not automatically red, flag.

How much messaging is too much messaging?

First and foremost, you must remember that the goal here is not to find pen pals but to physically meet someone and hopefully form a relationship.

Since the goal is to actually meet someone, you must find the sweet spot between introducing yourselves to each other on the one hand, and established the relationship as an online one on the other. Unless you really do just want pen pals, then by the second or third day of messaging you must start suggesting how nice it would be to meet up.

If you find yourself messaging this person for hours on end then it is definitely past time to set up that physical meeting. While you want to get a sense of one another, you do not want to go to a first date with nothing left to talk about. Furthermore, while it may sound counterintuitive, you do not want to get into an online friendship. People have a natural tendency to label and classify and if you chat online with each other for weeks, you will find that when you meet physically that the interaction feels awkward or “off” because it is not the interaction the two of you have become accustomed to.

Finally, lets be honest: people usually use their very best, very most made-up, thinnest, most attractive photographs for online dating. If you spend weeks chatting with those pictures in your mind, then you risk disappointment when you finally meet and being disappointed may lead you to overlook someone who, while a bit less stunning than your imaginary chat partner, could change your life if you just let them.

The naughty stuff!

So you and your prospective date are happily messaging, you might have already set up a casual date for a few days hence, you make a slightly racy double entendre about cuddling on the couch and they take the bait. They coyly ask what you mean by “snuggling.”

This is both good news and bad news. The good news is that they are definitely interested in you, and they would seem to have the same physical needs you have. Here in the twenty first century, both men and women can be fairly blunt about what they want, who they want, and how they want it.

The bad news unfortunately is that this is not the time or the place to take your nascent relationship to a quasi-physical stage. If you think that not having anything to say at your first date is awkward, then imagine how awkward it will be if you’ve spent the last several nights before meeting getting your keyboards sticky. It will not go well when it comes times to sit across from each other in a coffee shop and have a normal conversation.

This is not to say that there is never a time to verbally push one another’s buttons, but only that before you have had a couple of dates is not that time. Keep your double entendres PG-rated and if they rise to the bait, then keep your responses vague and mysterious. “You’ll just have to find out” will get you further in the long run than graphic detail.

This goes absolutely triple for exchanging pictures with one another. The goal is to actually see and do things with one another, not talk about it and show each other. While it may be difficult to resist if it seems to be available, it will work out much better in the long run if you deliberately progress through communicating, meeting, and then the naughty stuff.

To summarize then…

The goal is always to meet someone physically. Anything else and you’re just pen pals, a status which is arguably worse than being placed into the friend category. At least a real friend might introduce you to other real people, even cute real people, but when was the last time you met someone’s pen pal? You must therefore strike the sweet spot between convincing them you’re not married, not a pathological liar, and not a serial killer like so many other online daters, and the point when you have gone too far down the road of chatting and texting and been labeled as an online friend. It is almost always going to be better to move towards a physical meeting earlier rather than later although there is no hard and fast rule.

Avoiding the bots and scammers is easy, you will develop effective radar for them within weeks of starting to meet people online; they just lack the time and intelligence to be really effective and if they are generally going to cut and run very quickly in favor of easier marks. What is difficult is getting those responses, building a rapport in a matter of days, not weeks, and convincing people to meet you out in the real world.

Have fun! Or more realistically, grow a thicker skin, develop a skill set, radiate confidence and worldliness, and persist until you get whatever it is you’re after. To succeed you must practice, experiment, and inevitably and repeatedly fail. Failure is good even if it stings. People who fail still get dates while people who don’t try don’t get anything.

Author Disclaimer: The views expressed in this article do not represent the views of the Social Security Administration or the United States Government. They are solely the views of Ted Stalcup in my personal capacity or as a representative of EmLovz. I am not acting as an agent of the Social Security Administration or the United States Government in this activity. There is no express or implied endorsement of Ted Stalcup or of EmLovz by either the Social Security Administration or the United States Government.