When you’re not sure if you’re on a date or not

There’s an episode of Friends where Ross keeps attempting to ask out a woman who has a kid that plays with his son Ben. She finally asks him over one night, only for him to realize when he arrives that she meant the invite in a babysitting capacity while she went out on a date with someone else. This might seem like a pretty extreme example of miscommunication when it comes to whether a date is actually a date, but actually it is not! There is sometimes a land of in between where we aren’t sure and it feels incredibly awkward to outright say, “hey is this a date?” So I’m here to tell you all that I have learned wending my way through the murky is it or isn’t it territory.

I was once spending time with a good guy friend of mine, and had developed a bit of a crush on him. One night we ended up kissing, which he initiated and to which I was completely receptive. Then we both went out of town for various reasons, I had a work trip and he went on a family vacation, our time apart overlapping and ending up being about three weeks total. When we were finally both back in the same city and made plans to hang out, I assumed it was a date and we would be picking back up where we left off. Instead he asked me if I had any suggestions for a nice place to go to dinner because he had met a girl on his vacation and wanted to take her somewhere special. AWKWARD!!! And may I also say, ouch?

But also, sometimes you’re the one who’s oblivious. Remember in SATC when Charlotte went out with the pastry chef she was friends with and he kissed her before she got in a cab and she was totally flabbergasted? That happens! When I first had the plan to take a cross country road trip, one of my coworkers suggested I email her son for tips since he had just returned from doing it. He and I traded emails and agreed to meet up one evening where he would lend me all sorts of guide books, show me his route maps and basically answer any and all questions I had about it.

We met up at a bar and he was immediately super helpful, showing me the itinerary he and a friend had made beforehand and where they had veered from it. Jotted down the best routes, possible alternatives if traffic or weather threw up any obstacles, as well as some must-see picturesque spots to hit along the way. An hour and a half later, I was happily gathering up all my new materials that I was borrowing when he asked me if for our next date, we could maybe go see a movie or have dinner. Caught off-guard, I stared at him, not sure what to say next. Neither of us had been flirtatious during the time we were hanging out, and I didn’t want to rudely shout “um this wasn’t a date”, so I just said “Oh I’ve got a lot going on right now, and this trip coming up, so I’m not dating anyone right now.” I could feel my face turning bright red as I said the words, and he looked distinctly embarrassed which made me feel terrible. But better than agreeing to go on a “second” date out of politeness!

Sometimes it is just straight up confusing. I have been someone’s date to a function, as well as brought someone as a plus one without any intention of romance on either side. But publicly calling that person your date has led to assumptions that the two of you are in fact dating. And then I’ve wondered if even though we were simply good friends up until this “date” does he think I’m trying to take it to another level? Am I subconsciously trying to do that? Is it just because we’re all dressed up and not in our usual comfort zone, something all of a sudden feels different? What does he think? Is this Dawson’s Creek syndrome when Joey wears a dress and makeup and sings a song? And will everything go right back to normal tomorrow, when I slip back into a hoodie and jeans? Sometimes I really don’t know and wish there was some way to casually say “hey is this a date? Asking for a friend.”

In my opinion, the easiest way to figure out if you want your hang out time to be considered dating, is noticing how you feel when that person isn’t available to spend time with you. And one of the identifying factors I’ve noticed when I’m not sure if a guy is inviting me on a date date, no strings hang out, or a friend date, is how plans get made. Is he taking my schedule into account? Calling last minute? Just inviting me out with him and his group of friends? These aren’t hard and fast rules, just a few things I’ve tried to pay attention to, when I feel I’m not sure what’s happening.

A friend of mine told me that when he’s not sure, he will try to make a playful comment like “does this qualify as a date” so that if the girl says no, it won’t be uncomfortable, and he feels he’s leaving it up to her to decide where things stand. I was once hanging out with a guy whom I really was into but wasn’t sure how he felt about me, so I started asking him what he was like on dates. His MO, what he liked to do, etc. He started to say “I don’t know” and then shyly said “well you know, what we do. Those are dates.”

And it occurred to me that the biggest lesson is, if you can’t talk about it, you probably shouldn’t be doing it anyway. It’s not always the easiest conversation to have, especially with someone you don’t know well, but it would probably save us all a lot of time and stress if we just asked the question. Even if the answer is “no,” isn’t it better to know, rather than wonder and dissect every intricate detail of what they’ve said and done as we vent to our best friends and try to figure out by committee what it all means? And if someone is asking us because they are unsure, let’s try to remember how we feel when we don’t know!

[Image via NBC]