Assuming that you have built a healthy degree of goodwill and camaraderie with this person over the course of these message exchanges, asking how long they’ve been single isn’t a faux pas in and of itself.
That being said, you shouldn’t take the fact that you have had multiple message exchanges with this person as your ticket to be too intrusive or invasive in how you go about asking this person questions.
You still don’t know this person.
You only just met them on a dating site.
There is so much more about this person that you don’t know.
Multiple message exchanges with someone can give you a false sense of security.
You get so comfortable that you start asking questions that the person isn’t quite ready to answer.
Relationship questions are particularly touchy.
The danger of bringing up this type of question too prematurely is in what it triggers in the person.
Those enjoyable text message exchanges suddenly hit a roadblock and the question asked is now testing this person’s winning personality.
You asked about how long the person has been single and it feels like you have just let the air out of the tires.
This person was having such a good time with you and you had to bring this up.
In and of itself, this isn’t a bad question.
It shouldn’t be a faux pas.
The thing is, you are still dealing with a human being at the other end of that keypad.
You have no idea what that person’s relationship history has been.
You don’t know where they are at emotionally when it comes to the idea of love.
Yes, you met them on an online dating site, but that doesn’t mean that they are ready to dive into talk of relationships over text messages.
For some people, this is a heavy question that easily brings up bad memories about a previous partner.
They did a lot of work on themselves to get over that relationship and you have reminded them about it.
It’s just a question.
It shouldn’t be such a big deal.
It’s just that you are dealing with a human being on the other end and human beings are complex.
Simply assuming that you can ask about how long the person has been single can be a slippery slope.
You are way over your ex.
You are a clean slate.
This person on the other hand doesn’t want to be reminded about their ex.
It doesn’t always mean that they haven’t gotten over the ex.
They just don’t want to be triggered.
It is akin to an alcoholic who avoids being around alcohol.
They have been sober for years but that doesn’t mean that they want to watch you gulping down a bottle of what used to be their favorite beverage.
They don’t want reminders nor the temptation to go back to a place that they never want to go back to.
In time, they could develop a strong enough resistance to be just fine if people around them are drinking alcohol, but they aren’t quite there yet.
You don’t want to trigger a memory in this person that could be unsettling to them to the point where it sours an otherwise enjoyable conversation.
To be on the safe side, avoid mentioning anything that could trigger a memory of a bad relationship or breakup.
There is more than enough time for that if the both of you hit it off and meet up on dates.
For now, keep your text exchanges light and fun.
Only engage in conversation in regards to relationships or singlehood if the person has given you an opening by volunteering that information about themselves.
Then you know that the topic is fair game.
If you like this person, don’t keep exchanging text messages into perpetuity.
Set up a physical meeting fairly soon.
Meeting face to face does a lot to build trust and bring down invisible barriers.
This makes broaching sensitive topics that much easier.