Dear Jess,

Here’s the skinny. I started a new job with these two guys who are friends. I really liked Guy A, who flirted with me from the start. But I was working very closely with Guy B.

One night we all hung out, and of course we started drinking. Guy A confessed that he had asked about me and was interested. But then he left the room, and Guy B kissed me (I was surprised!). I pulled back at first, but then I let it happen.  I was pretty sure that Guy A saw it.

The next week, things were back to normal – I was still flirting with Guy A, and he was flirting back. In fact, we went out for coffee. Then we all went out for drinks again. And affected by the whiskey, I texted Guy A and said that I liked him a lot. He didn’t text back. Instead, as we all stumbled outside drunk, Guy B tried to kiss me again! And I pulled away. But then we kissed. And I’m almost sure that Guy A saw it again.

I like Guy A so much, in a sincere way. I still catch him staring at me at work, and we have great conversations. But…I fucked things up, huh? Did I miss my chance? How can I show him that I’m interested in him, and that kissing his friend was a mistake???

(And don’t tell me to stop drinking! Because I don’t, which is why the few times I hung out with them, it affected me so much.)

Love,

Mostly Sober Sally

Dear MSS,

I have some advice for you, but I’m not sure if you’re going to like it!

But before we get into that – for anyone reading this and thinking, “MSS should know better than to get involved with co-workers!  It only leads to disaster!”  Blah.  Blah.  Blah.  If she was romancing a boss or subordinate, then yes, of course, the power dynamics become tricky and possibly immoral.  But getting involved with her colleagues?  Please.  Everyone knows that it’s dangerous to fall for people at work, but we all do it anyway!  Many of us spend so many hours at our offices that it becomes inevitable that our social and romantic lives will center around our cubicles as well.  Workplace romances are just a fact of the post-dating world, so to lecture otherwise would be a waste of time.  Nothing wrong with having a few Career Boosters on hand!

Moving on.  MSS, your story reminds me of a dah maxim that Becky and I repeat to ourselves all the time – You Keep Your dah In Check.  (There are more maxims where that came from, but you’ll have to wait for the book to read them!)  We can’t get greedy with our dahs!  Attention from guys can be addictive, and when one guy makes us feel special, sometimes we have a counterintuitive reaction. Instead of feeling fulfilled and satisfied, we suddenly feel sexy and vibrant and want five other guys to make us feel special as well.  Yet women with successful dahs tend to avoid coming across as players because they know that dahs Gone Wild is never a good look.  Yes, you may rotate from one guy to the next.  But you should give each of them your full attention when you’re engaging with them, and make sure not to shove the other guys’ existences in their faces. You don’t have a dah so that you can make guys jealous; you have a dah so that you can figure out what you ultimately like and want in a guy (and have a little fun in the process, of course).

But let’s be honest.  It’s a little late for that lecture, isn’t it?!  So what can you, MSS, do about this?

Here’s the tough love advice.

If you really, truly like Guy A, and you really, truly feel a connection there…then you need to be honest and communicate with him.  You need to put aside all the post-dating ambiguity (even though we’re usually all about harnessing that ambiguity), and tell him how you really feel.  Something along the lines of getting him alone for coffee or catching him by his desk at the end of the day and saying, “Hey, Guy A, can we talk for a sec?  I hope this doesn’t sound weird or presumptuous, but I just wanted to talk to you about what you may have seen happen between Guy B and myself.  He’s a great guy and obviously we get along really well, but here’s the thing: I actually really like you.  In a way that’s probably not all that smart, considering the fact that we’re co-workers, but whatever.  And I’m not saying that to put any pressure on you or on us, but in light of what happened at the bar last week, I thought you should know.  I think you’re awesome.”

I know.  Ahhhhhhh!!!!  Holy crap.  That sounds terrifying (at least while sober).  But consider it your penance for getting yourself into this sticky situation.   We’ve all been there – but honestly, most of us aren’t gutsy enough to try and fix our mistakes.  There are moments in every relationship when someone needs to cut through the crap and actually say how he/she feels, and this is one of those moments.  Don’t rely on small, ambiguous gestures to fix this for you – they may be easy, but they leave too much space for interpretation and, while you’re figuring out your next flirty email or sidelong glance, someone else may snatch him up.  Make the grand gesture (it’s really not even that grand!  he’s already admitted that he likes you!).  Your Guy B makeout session may have put you at a bit of a disadvantage, leaving Guy A to wonder if he can trust you, but you should think of this as an opportunity to push your relationship with Guy A to another level by being open and honest and real.

Why go through the potential awkwardness and rejection?  Because as I’ve said, if you really have feelings for someone, then you should do everything in your power to try and make it happen.  True connection is rare, and when you find it, you should beat dead horses into the ground trying to see if it can actually work.  You’re lucky to have fallen for Guy A, so don’t let that go simply because you fear rejection or think he may have gotten the wrong idea after seeing you with Guy B (he probably did – that’s why you have to set him straight).

WTF?! BOTTOM LINE:  Don’t worry – you haven’t missed your chance to show Guy A that you like him!  But you have to act now.  Avoid miscommunication and ambiguity and tell him how you feel.  While sober.  Tell him that you’re interested, and see what he does with that.  If he likes you, it’ll be on.  And if he doesn’t, then at least you’ll never harbor any regrets about what could’ve been.

Before I sign off, there’s one more part of your story that needs to be addressed.  You’re so into Guy A, but you kissed Guy B on two separate occasions.  Oh sure, he kissed you, and then you pulled away.  But both times, you then “let it happen.”  So let’s focus on him for a second.  Are you really getting that drunk?  Is he functioning as your Ego Booster, showering you with attention when you feel jilted by Guy A (although there wasn’t too much jilting going on in your story)?  Or is some part of you attracted to him in some way?  You don’t seem to regret kissing him, other than your concern about Guy A seeing it happen.  Perhaps you’re subconsciously thinking that maybe Guy A will like you better if he sees you making out with another guy?

(If that’s the case, stop right now! That line of thinking is wrong.  He wants to know that other guys find you attractive, absolutely.  But he doesn’t actually want to see it.  Trust me on this point.)

You may want to consider the possibility that maybe, just maybe, you’re not ready to be in a monogamous relationship right now.  Despite being sincerely interested in Guy A, your actions may purposefully be showing him that you’re not sure what you want yet.  Which is totally fine!  The beauty of the post-dating world, and Dating & Hookup, is that it gives you the time and space to figure that out.  But if that’s the case, then it’s probably not worth pushing something more serious with Guy A right now, just to screw it up down the line because you weren’t actually ready. At that point, work will become a nightmare.  So think about why you’ve been publicly engaging with Guy B, and if that strikes a nerve…then I would recommend pausing for a moment, and letting all the pieces fall where they may while you figure out what you truly want.