Dating Advice from Me and LiLu

My Dear Restaurant Refugee,

I am that cliché, long time reader but first time commenter (or emailer is more accurate) and I was wondering if you’d give me your opinion on something.

I work with a guy that seems to be a lot like you – smart, good looking, well dressed, and pretty comfortable around women.  I wanted to use International Crush Day to tell him that I’ve been crushing on him for a while, but he was out sick that day.  I’ve kind of lost my nerve since then.  What’s the best way to approach him?  Our office goes out sometimes for happy hour and such but I would never make a move in front of other people.  I’m pretty sure that he’s single and straight but don’t know what to do next.  Help me.

Afraid of Unrequited

p.s. I also wrote to Carolyn Hax, but I am pretty sure I have a better shot at getting a response from you.  If she responds too, I am probably going to ditch your advice in favor of hers.

Dear Afraid of Unrequited,

First, I thank you for reading and taking the time to write me this email and for your very kind words (ed. note: I did ask AU’s permission before using this as a blog post.) I am always flattered and humbled by the notion that people would ask my advice on anything.  As always, it should be noted that free advice is frequently worth exactly what you pay for it.

You don’t indicate how directly you work with this gentleman and that matters a great deal.  You also don’t indicate how big your organization is.  I am going to assume that this chap is neither your direct boss nor one of your reports – sexual harassment is never sexy.  If he is either, you need to put the crush down and back away… quickly.  The same thing applies if you two work in a really small organization or small office of a larger organization.

Your fear and hesitation is rooted in an aversion to rejection.  Everyone has it, men have just gotten more accustomed to dealing with it than women because of societal mores that have men deluded into believing that we almost always make the first move*.  The larger and more realistic question is what are you afraid of?  If you invite someone for drinks and they say no, what’s the big deal?  They have done their worst and said no, but what does that no really mean?

If the worst case scenario is a poor reaction followed by gossiping to coworkers, is that a guy that you would want to date?  From what you wrote, that seems an unlikely outcome, but if it did occur I would consider it a dodged bullet.

Some might consider a public and messy break-up that creates an untenable work environment the worst case.  I consider that situation the cautionary consideration to other questions: should I have sex with him, should I get serious with him, as those are two questions that can not occur without a first date.

My advice:

  • As with any dating issue, consider the potential risks and rewards.  The risk here is relatively low, so just ask him already.
  • Choose an activity of mutual interest (gallery opening, new bar, billiards, whatever) and issue the invitation.  More than a week in advance can lead to heightened expectations, over-thinking and the like; two days or less can seriously reduce the likelihood of his availability.  Four days feels juuuusst right.
  • If he says no, don’t over-analyze** his answer.  Do pay attention to what he does.  You’ve made it clear that you’d like to socialize with him outside of the office.  Even if he is among the breed of men who needs to be bashed about the head with a flirtatious club before he understands that someone is interested, you extended an invitation.  If he wishes to see you in a non-working context but cannot on this date, he will reciprocate the offer.  Whether or not he reciprocates your affections, is another question.
  • Do not allow or initiate any physical contact (kissing counts) until you have an all-caps NEED for it, until you cannot imagine the earth rotating even one more degree without it.  It is throwing your cap over the wall in an office environment and you better NEED it before you go flinging it.
  • Don’t create an evidence trail.  Email might be an easier way to ask but resist that urge.  If you do make plans / start dating / get serious / whatever, do not send flirty emails via the office network.  This applies to office cell phones, voicemail too.  You must erect an emotional firewall between your professional interaction and your personal.

However you choose to proceed, please let us know what happens.

Best of luck to you,


* 96.34% of the times a man “makes the first move” it’s a reaction to something subtle and deliberate that a woman has done to give us permission to make the nominally inaccurate but perceived first move.

** notice a pattern developing here?

For a woman’s perspective on this question, I turned to my dear friend, LiLu for her thoughts…

Dear Afraid of Unrequited:

I must admit, my first response is NO, BACK AWAY FROM THE COWORKER, DO NOT PASS GO, DO NOT COLLECT $200.

This reaction may or may not come from personal experience. *cough*

That said, it sounds like you want to go through with this, one way or another. So, (sigh), let’s figure out the best way to do it.

Eons ago, back when I occasionally exercised my own feminine wiles, my Plan of Action probably would have looked a little something like this.

Let’s call it…

The “SCORE” System, a la LiLu.

Step 1: “S” is for Stalk.

Stalk the hell out of him. Facebook, Twitter, Google- do what you have to to find out that he is IN FACT straight ‘n single. (A little research never hurt the cause, neither.) There is nothing worse than batting your eyelashes at the Christmas party only to have his less-than-approving girlfriend- or boyfriend, for that matter- take his arm and proceed to kill you dead with eye lasers.

Trust me. They burn.

Step 2: “C” is for Corner.

Corner him at an office happy hour. Get some alone time! Wait until he goes up to the bar, and “remember” that your own drink is empty, too. (After you down it. Duh.) Finagle the seating so you’re both on the end of the table, affording you some privacy. Last ditch move: arrange for some friends to be at a bar next door, and casually suggest he come with you for “one more” when the office group breaks up. Do what it takes, my friend. Get Creative. (Oh, look! Another “C”!)

Step 3: “O” is for Obvious.

Look. Dudes are dumb. I’ve said it, Refugee’s said it… while we have to consider the possibility that this may be a case of He’sJustNotThatIntoYou-itis, because the workplace is involved, there’s no way to know for sure. He could be reluctant to date a coworker; he could be your average dude who is completely effing clueless that you’re interested. So, once you’ve cornered him, make your affections obvious… while leaving him a “Get Out of Jail Free” card all the while. That way, you can both pretend it never happened.

You know, after those first five or so awkward meetings at the copier.

Step 4: “R” is for Read.

Read his response. For the love, try to be objective. Do keep in mind that you are trying to save yourself from having to suffer through eight hours of utter humiliation EVERY. DAMN. DAY. Look for encouragement, watch for disinterest. Pay attention to whether he asks about and listens toyou, or whether he talks about work or {insert other purely platonic subject here} the whole time. Huge, red flag signs of interest are the following:

  • Any on-purpose touching. At all. This clearly crosses a boundary between coworkers. You win. (Well, halfway. He at least wants to get in your pants.)
  • Insisting on paying for your drinks. This is an easy way for him to show interest/make your interaction more date-y, especially without alerting other coworkers.
  • Inviting you to a future anything. See phrases like: “This was fun, we should do it again.” “Have you ever been to XYZ Bar? We should go sometime.” “Want to go to a Pants Party next Friday?”

Just kidding on that last one. Don’t answer that.

Step 5: “E” is for Execute.

Now, depending on how Step 4 goes, you might be “executing” your future forever Entanglement as lovers… or making an entirely mortifying tail-between-the-legs Escape.

I warned you.

Good luck!


ood luck!



20 Responses to Dating Advice from Me and LiLu

  1. kitty says:

    alternatively, just send him this link.

    That might work too… but then there is that whole evidence trail thing.

  2. I like kitty’s advice above.

    I am not willing to entirely endorse the passive aggressive approach.

  3. Jean says:

    Dig the advice. I am so glad I’m not her though. SO GLAD.

    You and me both. There have been times when my no office dating policy was tested… but I’ll keep those stories for another time.

  4. Wow. What fantastic advice. Did LiLu really make up an acronym for dating?? And it’s SCORE??? Ahhh, that lady. Too much.

    That is the kind of thing that establishes just the type of funny that LiLu is. She is just that way… and her advice was spot on.

  5. magnolia2010 says:

    scary, scary, scary – office dating is almost never a good thing. it’s weird enough to work with someone you were dating before you started at the company (done that, never doing it again). i think it’s just too big a risk. but i’m in law school, so i am probably the most risk-averse person on the planet. 🙂 nevertheless, all this advice is a good roadmap to do something that scares me to no end. proceed with caution, AU!

    Walking into a meeting and seeing last night’s drunken mistake sitting across the table is never a comfortable thing… not that I have ever done that *cough*. Risks averse and necessary vulnerability are incompatible – food luck with law school and the rise aversion.

  6. Alice says:

    dated a coworker at my very first job, at the tender age of 22. or 21. whatever: i was young and stupid. MAN OH MAN did that end badly. do not recommend!!

    I once had an office fling that was the perfect kind – we got together at the happy hour that was my going away party. Other than that, I am not a fan.

  7. […] Head on over to read about the “S.C.O.R.E. System,” a la LiLu. And add your 2 cents while you’re at it. […]

  8. cari says:

    nice. i like it for sure.

    i’ve never dated in an office (or any other kind of coworker) environment. mostly because i’ve only really ever worked with girls. so i can’t say that i have MUCH to offer here.

    however, one thing to remember is that even if he’s not interested, it’s NOT the end of the world. you are who you are, with or without him. keep that in mind and you’ll do just fine. 🙂

    Getting to the No is just fine. Rejection sucks, but we still make too much of it. Ask the question, accept whatever answer and move-on. Neither petitioner nor respondent need make a big deal out of it.

  9. Meghan says:

    Between the advice of RR and Lilu I’m certain to have a date or restaining order by the end of the week. Thanks guys!

    In that case, we expect to hear back from you by Friday.

  10. Jo says:

    I did this once. I have imaginary balls of steel and actually just walked up to a coworker I’d been flirting with for a while and asked him out. He replied “I’m flattered, but you’re not my type”

    Man, those next couple of weeks sure were awkward, but I learned my lesson and never ever crushed on a coworker.

    Sorry, but that co-worker engaged in unnecessary and excessive truth which makes him either socially inept or a tool. Having the pleasure of knowing you a bit, I also think that it was his loss. This was one of those situations where a minor omission or even a little-bitty-lie would have been preferable to the subtext of “you’re not my type” rattling around in someone’s head.

  11. notsojenny says:

    i dated a coworker.
    we worked in the same dept., different teams, different floors… but with all the same people and sometimes interacted for business purposes. hiding it was actually the fun part.
    he’s my husband now. it’s not always going to end badly… but often it will.

    Sometimes it does end beautifully and I am happy that it did for you… and I imagine a shared secret helps bring a team closer.

  12. gennarae says:

    My theory is: “You don’t get your meat where you get your bread.” Unfortunately, it wasn’t my theory when I was 22. Burned and learned.

    So I’ve been shopping in the wrong places all these years?

  13. Kristy says:

    Excellent advice by the both of you. And the SCORE system is gold. We need some follow up on this. It’s sure to be interesting.

    You have to love concept that comes with it’s own mnemonic acronym.

  14. Cheryl says:

    My dating life got so much better after Facebook and I found each other. Now I can stalk however I please!

    As someone who refuses to share via Facebook, I can’t quite relate but I understand how you feel.

  15. brad says:

    The need it before you go for it advice is a winner. Sounds like the best way to avoid regrets.

    I think that the really need it before you start it is a great idea for most kinds of relationships.

  16. BigMamaCass says:

    LMAO Fantastic advice. 🙂

    Thank you, glad we could help.

  17. JerzeyGrrl says:

    As I am a woman and not terribly tuned into how guys think (go figure), the point/counterpoint was appreciated. Also, a great way to start my day. Snaps to both of you.

    I am lucky enough to have a friend who was capable of providing such a brilliant counter-balance to my male, and older advice.

  18. spleeness says:

    Fantastic advice – both counts. I really like the tidbit about paying attention to his signals (after all the stalking, lol).

    All people tell us precisely how we should treat them through their actions.

  19. lemongloria says:

    Excellent advice! Definitely want to hear where this goes.

    I am looking forward to the follow-up too.

  20. […] the by, I received an email update from Afraid of Unrequited.  She took some of my advice, some of LiLu’s advice, and stepped in a couple of the traps about […]

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