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 toward 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 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 even 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 them, 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,’ even, are taboo words and they make people nervous,” said Thomas Edwards, a professional wingman. “To alleviate that anxiety, they use softer words like ‘let’s hang out’; it makes everything a bit more casual but also confuses the intention.”
Meetups with co-workers, friends or acquaintances from clubs or organizations can sometimes fall into in this middle ground between a date and not. There might also be more at stake if the intentions are expressed poorly, as compared to 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?” Edwards says. “You must be clear, transparent and honest, because without that, things get very complicated.”
Intentions can become an especially serious issue in an era when 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 their intentions, they might make the 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 nonaggressive, undeniably romantic, well-intentioned way, can be tricky,” says 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.
Even when no one intends a surprise date to be manipulative, they can come across that way. If simply asked to eat dinner together, without the implication of a date, many people might say yes in part because they thought they were safely out of “date” territory.
“At its best it could be an awkward situation for the person to gracefully bow out of,” Kali Rogers, founder of Blush Online Life Coaching. “At its worst, they could easily feel like they’re being sexually harassed. It’s best not to put somebody you like in either of those situations.”
And if you do find yourself on a surprise date, then once the mental fog clears, it’s important to remember you always have a choice.
“It is more than acceptable to end the date immediately,” Rogers said. “You do not need to continue being put in a situation you did not agree to in the first place.”
“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,” 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. House describes smaller moves toward 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. You are dropping little thoughts in her mind that will unexpectedly pop up and make her start to see you from a new perspective.”