WASHINGTON • Five years ago, I became good friends with a gentleman in my beginner dance class. We had good dance chemistry, so we would go to multiple classes and open dance sessions each week.
We weren't "together", but we'd check in and see if the other person was going and dance with each other frequently. These meet-ups weren't dates and didn't feel like them, but after a few weeks of this, my dance partner asked me to get dinner instead, without any further explanation.
I had entertained the idea of a romantic connection early on in the dance friendship, but as we remained platonic for weeks, I had closed off the possibility in my mind. This dinner seemed too late to be a move towards romance, especially given that I was moving away within a few weeks.
We ate at a romantic outdoor restaurant and got entirely off the subject of dancing, talking instead about our families and other personal topics. I found myself asking outright whether it was a date or not, and I got a pretty confusing answer: "I don't know."
The confusion was eventually cleared up through a few multi-hour talks: We weren't meant to be in a romantic relationship and the timing would have been terrible even if we were.
Part of my concern with dating him was the confusing way our relationship would have started, especially since it made me feel like he wasn't interested enough to make a clear move. And this confusion also ended up having a chilling effect on what was, otherwise, a good friendship.
This kind of "surprise date" - what I call a social outing that turns out to be a date, even if one or both parties don't know it beforehand - can seem innocent enough and perhaps exciting to some people.
But to me, it seems like a way to risk making a friendship uncomfortable or making someone feel like you don't really like him, even if you do.
Dating apps and a pick-up line in a bar clearly signal a person's intentions as romantic. Unfortunately, if those intentions are clear, it allows us to avoid the words "Want to go on a date?" and so we aren't used to stating what we want in ambiguous contexts.
"The words 'date', 'romance' and 'sex' are taboo words and they make people nervous," said Mr Thomas Edwards, a professional wingman. "To alleviate that anxiety, they use softer words such as 'Let's hang out'. It makes everything a bit more casual, but also confuses the intention."
Meet-ups with co-workers, friends or acquaintances from clubs or organisations can sometimes fall into this middle ground between a date and not. There might also be more at stake if the intentions are expressed poorly, as compared with a casual first date arranged on Tinder.
"You have to ask yourself: Is the prospect of having a romantic relationship more valuable than the risk this poses to the current relationship?" Mr Edwards says. "You must be clear, transparent and honest because, without those, things get very complicated."
Intentions can become an especially serious issue in an era when Hollywood film mogul Harvey Weinstein and other men accused of sexual misconduct have allegedly tried to initiate physical contact in encounters that were purportedly business-related. Even when nothing illegal is happening, when someone creates an atmosphere of romance without voicing his intentions, he might make the other person uncomfortable.
Given these complications, specifically saying, "Want to go on a date?" can be useful.
"Doing a surprise date, even when done in a non-aggressive, undeniably romantic, well-intentioned way, can be tricky," says Ms Laurel House, a dating and empowerment coach. She mentions that it might work for rekindling a relationship with an ex or for making the person you're hooking up with more of a long-term romantic partner, but in both of those cases, some mutual interest was expressed already and she recommends moving slowly to make sure the other person is on board.
If you do find yourself on a surprise date, once the mental fog clears, it's important to remember you always have a choice.
"You are adults and can communicate with each other; it can be hard to say, 'I don't feel the way you do', but it's necessary," Mr Edwards added. "Then you can collaborate on whether to continue with the planned activity."
While there are other strategies to finding out if these friends or colleagues are interested in dating - like getting a friend to ask the person subtly or observing whether this person gives you more attention than other friends - the main rule of thumb is more communication rather than less.
And sometimes, holding off on the date can help. Ms House describes smaller moves towards a romantic relationship as a better way to go, with simple compliments and kind gestures to start.
"You are planting little seeds that will hopefully root down and grow up," she says.
"You are dropping little thoughts in her mind that will unexpectedly pop up and make her start to see you from a new perspective."
• Leavitt is a teacher and writer who focuses on travel, personal finance, relationships and food.