How to Know If You Are Actually ‘On a Date’

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Ryan O’Connell is a New York-based writer. He likes shoegaze, the Olsen Twins, and figuring out why people do the things they do. Oh, and he tweetsCheck back each Thursday for his latest Call Your Boyfriend column. (You KNOW you have a question. Send it to Ryan.)

Hey BF,

This might sound crazy/weird but whenever I meet someone new and they ask to hang out, I can never tell if I’m on a date with them or if we’re just grabbing drinks as friends. Help!

-Friend Or Ho

Hey Friend Or Ho,

You’re not crazy. I’ve been in this situation more times than I’d like to admit. I’ll meet someone at a bar and they’ll be like, “We should hang out sometime!” Which, of course, I take to mean as, “I’d love to have sex with you and be the (other) father of your children someday.” So I go and meet them thinking that this is definitely a date with a capital D. Like, we’re going to have drinks, we’re going to laugh, we’re going to cry, and then we’re going to dry hump in front of my apartment before kissing each other goodnight. Unfortunately, more often than not, I am DEAD wrong and it turns out this invitation for drinks was strictly platonic. We talk about our exes during the evening (first sign that it isn’t a date), we mention someone we’re currently dating casually (ouch! death to romance!) and then we hug goodbye. Meanwhile, I feel like an idiot for thinking all along that the encounter was something else. I’m embarrassed for having told my friends, “OMG, I’m going on a date tonight!” when it was really just like any other hangout. I guess we’re all just friends until proven date-worthy?

To make sure you don’t end up awash in a sea of confusion, you need to be honest about your intentions from the get-go.

It’s time to put this deceptive practice to rest once and for all. Look, there is nothing wrong with going on a friend-date with someone. You’re totally allowed to meet a person of your preferred gender and not want to have sex with them. At the same time, however, I feel like people ask each other out (with the intention of it MAYBE being a date) and then deliberately avoid the date label JUST IN CASE they turn out to be not that into you. It’s like insurance for a bad night out. “Well, I shouldn’t feel pressure to kiss you goodnight because this was never a date! Unless you were totally awesome and I clicked with you instantly. Then it was totally a date!”

The fact is that dating is hard these days. Hell it was hard 50 years ago — it’s still hard. That’s why there are advice columns like mine, even though I’m certainly not perfect either. When I went out with these guys for drinks, only to realize that they weren’t a potential love interest for me (or rather, I wasn’t for them), I didn’t say anything about it. I didn’t use the word “date” with them before, during, or after the event. I never said what I wanted. I never let them know what I was really after, because I was too scared. I was part of the problem.

So here’s the deal: to make sure you don’t end up awash in a sea of confusion (and it WILL happen again, I assure you), you need to be honest about your intentions from the get-go. And if you find yourself on the pseudo-maybe-date wondering if it is in fact anything romantic, ASK. “So, like, are we on a date? Because I’d like to be.” If you need a drink or two before saying it, knock yourself out.

I finally did that with one of the hedge-your-bet dudes, actually. After our first non-date, I texted him and was like, “Hey, I’d love to take you out sometime. Let me know.” And then he gave me this kind of half-assed yes, which informed me that I would never be seeing him again. It stung to get rejected (it always does) but at the same time, I was tired of being surrounded by ambiguity. If you want “drinks” to mean “date” then let them know that. Send them implicit or explicit messages that let them know that you have no real interest in being their friend. You want something more. Otherwise, it becomes your fault just as much as theirs. HONESTY!!!!


So here’s the situation. I went out with this guy a few times who I thought was single. These “outings” sure felt very similar to dates, and I assumed he was into me. Then, he drops the bomb that he has a girlfriend. WTF? Part of me wants to tell him, “Yo, you could’ve told me that four cute dates ago!” but I don’t know if I have the right. Even though I feel like he was purposely withholding information from me, I’m not sure if I should confront him about it. What do you think? Was he leading me on?

– Single Until Taken

Hey Single Until Taken,

I hate to say it but it sounds like you’ve been Jack Berger-ed. Remember him on Sex and The City? He was the guy who dumped Carrie via post-it []. Well, long before all that went down, he and Carrie met and went on that cute daytime date together. Things were going great until Berger casually mentioned to her that he had a girlfriend. Oops!  Carrie was stunned. Weren’t they just on a semi-date right now? How could he have been in a relationship?!

Yeah, you’ve definitely been Berger-ed. It’s okay, though. I’ve been Berger-ed as well.

A year or two ago, I went out with this boy I’d met eight months earlier in San Francisco. I liked him the second I saw him, mostly because he was a Mexican babe and a writer (AKA my type one hundo percent). That day, we talked for a bit and as fate would have it, I learned that he was just visiting SF and actually lived in Brooklyn. Hot dog! We made plans to hang in NYC once we were both back but, unfortunately, when I reached out to him, I got no response. Oh well! Moving on, I guess!

Cut to: A few months later. The dude starts blowing me up on Facebook chat telling me that he wants to hang out. At first I was like, “Where were you eight months ago, mister?” But then I thought about how cute and nice he was, and got over it.

Ask, do you intend on seeing this guy again? Do you care? If the answer is no, then fine. Tell him how you feel. BE HONEST.

We met up for drinks and ended up having a gay ol’ time. It wasn’t a date but it wasn’t not a date, you know? (Ah, there it is again. The #NotClear Date.)  We chatted mostly about relationships and college and California. He told me about how he used to do online dating a few months ago, but quit because he kept on meeting people he hated. I left our hang out session feeling good. The conversation had flowed pretty nicely and there was some flirtation. We talked about meeting up again when we said farewell, and the over next few days we G-chatted all throughout work, making jokes and being cute. It was definitely the Internet equivalent of a handjob.

Then, after a few days of constant G-chat foreplay, he casually mentioned to me that he had a boyfriend. WHAT? Now look, I wasn’t totally thinking, “OMG, he wants to date me” or anything like that, but he just seemed so…available. And when we hung out, he had a MILLION opportunities to drop the BF bomb on me but he didn’t, which made me feel like he had kept it from me on purpose. Like maybe he wanted to feel things out with me first and see if I was worth a forbidden smooch. I don’t know! Regardless, I felt like I’d been led on. I’m not saying that if you have a boyfriend, you shouldn’t be allowed to make new friends. Again, making friends is A-OK. Really! Still, out of fairness to the single party, you MUST somehow mention that you’re in a relationship the first time you hang out. Otherwise, you can’t blame a person for thinking that there’s romantic potential.

So yes, this man you went on a few “dates” with probably did lead you on. Should you confront him about it? Depends. After I got Berger-ed, I ignored the guy’s messages because I knew there was no way I could be “just friends” with him. The attraction was too much. I did think about calling him out on not telling me about his BF from the beginning, but in the end it wasn’t worth it to me. He could’ve easily just been like, “I was never flirting with you!” and then I’d look delusional, even if that wasn’t the case.

Don’t use me as a model though! (If you need a reason why, well, read my past columns.) Instead ask, do you intend on seeing this guy again? Do you care? If the answer is no, then fine. Tell him how you feel. BE HONEST. Screw it. People in relationships need to stop toying with our emotions anyway! They know we’re vulnerable. Why can’t they just leave us alone, for god’s sake?!

Check back each Thursday for his latest Call Your Boyfriend column.  You KNOW you have a question. Send it to Ryan.