Work Friend to Girl Friend?
August 21, 2011 5:57 PM   Subscribe

WTF Filter: "Working" with someone that I think there's more with there...but I don't know how to approach taking the leap. Not that special snowflakery inside.

Giant brain dump ahead. You've been warned!

I met this person ("Gina") at a networking event/nerd party a year ago. We casually tossed around working on some project together (she's in a different, but complementary field to what I do). My partner/hired help at the time did some Bad Things (business-wise, and without my knowledge), and subsequently, Gina and I didn't speak beyond the occasional pleasantry via social media here and there.

Fast forward 8 or so months, and she caught wind that the old partner was out, and I had new help. She had a project she wanted my input on, and so we meet up and discuss work things for a bit, and long story short, we have hung out in person 9 out of 10 days since. The days we haven't, there have been video conference/phone calls. Only about 5% (if that) work-related.

We go out to dinner, movies, other activities together. I've stayed the night at her place (in her bed, cuddled up and spooning), we've gone on a overnight trip out of town together (same bed situation). She's changed clothes in front of me (without the "hide your eyes!" comments). She's met part of my family, I've met part of hers (both of our families are out of towners). We've held hands, and done all the sorts of things that you see couples do short of actually kissing.

She has commented often about how I'm the first person she usually makes contact with in the morning, and the last person at night. If I haven't texted/chatted her by noon, I can guarantee she'll ping me. When I go to a public event, it's often assumed (by her) that she is going to come along.

If I were to look at this outside, I'd absolutely assume "these kids are dating". Almost every friend that has seen us together has assumed and commented to me that they think the same way.

Now, on the flip side. She recently (a month or so) broke it off with another guy. His lifestyle is such that he will never, ever be in the same city more than a couple of days, barring a death in his immediate family (this is why they split). The relationship they had was just a shell for a few weeks when she finally told him it wasn't going to continue.

When we started hanging out, she knew that I was on eHarmony and OkCupid (hey, can't catch one if you don't put out some lines, right?). I've since occasionally checked, but these are pretty much on autopilot. I only bring this up because at some point, she commented on how she could write an awesome profile for me. She randomly comments on a guy's looks (she's athletic and has a thing for soccer players), but I'm confident that she would never date based on looks (I've seen pictures of the last couple of guys; not lookers at ALL). She occasionally comments on how she would make an awesome wingman for me.

When things first started to simmer, and I thought there *might* be something there, I casually mentioned in passing that "$mutualfriend thinks we're dating, you know." She responded that she would probably never date someone she worked with. This was before things started getting very girlfriendish, so, it is what it is.

tl;dr, our "working together" is a pretty non-existent thing. She's brought me one (very small) project over the span of 3 months, and 99% of what her business could bring me is such small jobs that they're honestly not worth my time. I wouldn't miss it. I would absolutely love to date her, even though we're different races (I'm white and she's Indian, but grew up in the US in a Americanized household) and religions (I'm a Christian and she is Catholic school girl gone Unitarian at worst, slack Catholic at best). I think she would want to date me, but I can't place what's hold either of us back from making the move.

Pick this one apart, MeFites. What should I do?
posted by chrisfromthelc to Human Relations (32 answers total) 5 users marked this as a favorite
What should I do?

Fucking kiss her.
posted by geoff. at 6:06 PM on August 21, 2011 [10 favorites]

She sounds like a lot! Uhhh. Hold off on dating her because I feel she gives way too many mixed signals. Not good.
posted by InterestedInKnowing at 6:07 PM on August 21, 2011

Huh, why don't you ask her what the deal is? If you can't talk to her, she can't be your girlfriend.
posted by aimedwander at 6:07 PM on August 21, 2011 [3 favorites]

Like you said, you are basically already dating this girl. If you hadn't already done things like stay over, spoon, and hold hands I'd tell you to kiss her. But seeing as how you've kind of backed into a quasi relationship with her, you're going to have to be more direct.

I recommend, "Gina, I like you. We get along great, we already spend a lot of time together, and I think we should make out. What do you think?"

For what it's worth, I was in a similar situation a while back. Great friends with a guy, we gchatted/emailed all day long, made dinner together, watched movies together, etc. Even spent the night in the same bed once because we ended up talking too late. Except we never so much as touched each other. And then one day he tried to hold my hand and we immediately started making out. It'll be 2.5 years come October. This won't go anywhere until you make a move (which, in your case, will have to be extremely direct to have an effect). So get to it!
posted by phunniemee at 6:08 PM on August 21, 2011 [2 favorites]

To me it sounds as if she wants you to make the first move.

All the wingman comments, helping with dating profile, and the such lead me to think she's checking how serious you are about dating someone who isn't her.

You should take the initiative and kiss her. Ask her on a serious date or do both!
posted by Sweetmag at 6:09 PM on August 21, 2011

Woo her, Boyfriend! sweep her off her feet one night soon on a fantastic date. Then kiss her!!!
posted by jbenben at 6:11 PM on August 21, 2011 [1 favorite]

Sweetmag is right. She is dropping Zeppelin-sized hints on you. Take one.
posted by adamrice at 6:14 PM on August 21, 2011 [3 favorites]

She occasionally comments on how she would make an awesome wingman for me.

When things first started to simmer, and I thought there *might* be something there, I casually mentioned in passing that "$mutualfriend thinks we're dating, you know." She responded that she would probably never date someone she worked with.

These two things are the only and I mean ONLY elements of your question that give me any pause whatsoever. Because of these two comments, I think you need to be very clear about what you want from her. Rather than just taking her out and trying to sweep her off her feet without her definitely knowing it's a date, I second phunniemee's recommendation of saying flat out that you want to make out OR saying flat out that you really like-like her and want to take her out on a real date.

However, I want to add a caveat about communication styles. If you don't feel like being direct is going to work for you, you could just try initiating the smooching and see where it leads. But at some point, you'll have to have The Relationship Discussion.
posted by pupstocks at 6:21 PM on August 21, 2011 [2 favorites]

Anecdata: I didn't know my now husband and I were for sure dating until he gently cupped my cheek and kissed me while we were out on a "date" - which turned out to be a Date Date.

Romance her! What do you have to lose here??
posted by jbenben at 6:29 PM on August 21, 2011

All: Great answers. Please keep 'em coming.

Here's a couple of additional (may or may not be relevant) data points. When we aren't in the same vicinity, she always comments about how she misses me. Literally, while I was typing out this question, she mentioned missing me at least 3 times. She pretty much always says she loves me when we're signing off or one of us is leaving (most times it sounds friendish, could be interpreted differently). Sure, friends say these things, but I can't recall ever having one that did it to this frequency or insistence.

Anyhow, please keep the answers coming. Thanks!!
posted by chrisfromthelc at 6:35 PM on August 21, 2011

My feeling is you've already done the hinting things and she's hinted right back what the problem is. So lay it out for her:

Tell her that you feel that you want to be more than friends or work colleagues with her, that you hope the attraction is mutual, and that while you understand that she doesn't want to date people she works with, a chance at a personal relationship with her would be something of such high value that you would be willing to sever your professional relationship. Make it clear here that you value your professional relationship, but you like her enough to let it go -- you don't want to denigrate your professional relationship, but build up the personal attraction.

Then you've asked her a clear question, and will get a clear answer. If the clear answer isn't 'Yes, we should start dating' then you need to take your relationship back to being professional and friendly, in the way that friends are friends rather than in the way that lovers are friends.
posted by jacquilynne at 6:36 PM on August 21, 2011

Jesus, just kiss her already. This thing is way too intense to continue as a friendship, so it either becomes boyfriend/girlfriend when she kisses you back, or she looks horrified and you know to invest your time elsewhere in a primary relationship that involves, you know, booty.
posted by DarlingBri at 6:36 PM on August 21, 2011

I actually disagree with most of the commenters. I think her actions point more toward an interest in being super close friends than an interest in a romantic relationship. Here's why:
  • The wingman comments. If I were trying to subtly hint to my male best friend that I wasn't interested in him, I'd likely do so by playing up how awesome it would be for him to find another person, who was not me, to date--and I'd offer to help.
  • The comments about attractive men. If I were still trying to subtly hint to my best friend that I wasn't interested in him, and my wingman comments weren't working, I'd make a point of acting interested in other people.
  • Changing in front of you like it's no big deal. This behavior says, "I'm really comfortable around you and I don't consider being undressed in front of you a sexual or sexy thing."
  • Platonic cuddling and sleepovers. Same as above. At least for me, if I were interested in someone, sharing a bed would be sexy and exciting, not something I'd do habitually like it was just the usual routine.
I could be wrong, she could be waiting (and hoping) for you to make a first move. That's just not how I read her behavior. I wouldn't randomly kiss her, if I were you (surprise kisses are nice if there's mutual interest, but oh, how I hate surprise kiss-attempts from a person I'm not interested in). I'd say something like, "I'd like to take you out on a real date--you know, the kind where we kiss at the end. What do you think?"
posted by Meg_Murry at 6:41 PM on August 21, 2011 [9 favorites]

I'm puzzled by the timeline. Was she doing the sleepovers with you (spooning, cuddling, undressing in front of you) before she broke things off with the other guy?
posted by jayder at 6:46 PM on August 21, 2011

All: Great answers. Please keep 'em coming.

Honestly, no one should give you another answer and you should no longer be reading this thread. Kiss her and see where this goes. Seriously, you're wasting time, go!
posted by Brandon Blatcher at 6:46 PM on August 21, 2011 [1 favorite]

I was in a situation kinda like this for a while. You definitely want to ask her what's up as soon as possible, because the will they/won't they isn't as cute IRL as it is on TV, and can actually kill things (did for me).

That said, changing in front of you/spooning sounds like some pretty weird signals she's sending you.
posted by sweetkid at 6:56 PM on August 21, 2011

When you say India do you mean the country of India?
posted by dgeiser13 at 7:24 PM on August 21, 2011

@jaydar, after. Probably at least 3 weeks before that happened. The physical things have slowly progressed.

@dgeiser13, Yes. Both parents were British Indians who moved here. Her mom (dad passed a while back) is a higher-up for a major corporation, and is very American. Gina is what you'd expect from a mid 20's American girl. Catholic schooled, soccer and field hockey, and watches reality TV. They participate in Indian culture/holidays for the sake of family still overseas, but otherwise, they're an average American household (whatever that is). As far as dating is concerned, she has dated and prefers white guys from what I gather.
posted by chrisfromthelc at 7:30 PM on August 21, 2011

I agree that you need to formally ask her out. While you may think you're basically dating, and I may think you're basically dating, there are those who don't think it's official until it's official, or who think that if you have to actually go to the trouble of officially asking for their company, you'll value the relationship more or something. (This is not a view I hold fwiw.) People with that view would also mentally respond to "$mutualfriend thinks we're dating, you know" with something like "uh, if you're not going to actually ask the question, I'm not going to answer it." So, I'd formally ask her on a date and if necessary also formally sever your work relationship as jacquilynne suggests.
posted by salvia at 9:06 PM on August 21, 2011

You *really* need to sit down with her and DTR.
posted by msittig at 9:01 AM on August 22, 2011

I am the girl in a similar situation (though without the spooning, holding hands and cuddling), and I wish he would just fucking kiss me already. Or bring me on an amazing dinner date and pay for it. And then kiss her. (If you feel awkward, you don't have to specify it's a date, but you do need to show very clearly that it's a really special occasion for the both of you).
posted by moiraine at 12:44 PM on August 22, 2011

This stood out for me: She randomly comments on a guy's looks (she's athletic and has a thing for soccer players), but I'm confident that she would never date based on looks (I've seen pictures of the last couple of guys; not lookers at ALL).

Are you implying that you're unattractive, or maybe that she might not think you're attractive, or that if she were dating for looks, she wouldn't be interested in you?

Because if that's the case, then I'd lean way towards agreeing with Meg_Murray, that she is loving having a super-close platonic guy friend.

However, I also sometimes use a strategy, when I'm trying to push a guy into making a move, or trying to get a clear indication from him about whether he's really intersted, whereby I will tease him or talk to him about his liking other girls or going after other girls, the goal of which being to imply that I am "so clueless" that he's interested in me and that I assume he's trying to go after other girls, and so he thinks he needs to ramp his shit up and make a big move. This works for me a lot, actually.

It's hard, and I think either way you will have to gird up your balls and make a move. Because, with very close but 100%-forever-platonic guy friends, I have spooned and gotten undressed and gotten all interested in their love lives, because it was completely understood that there was nothing between us. On the other hand, it would take me a lot to get to that point with someone and another part of me is like, no way would I let a guy spoon with me unless I were interested in him romantically, because I wouldn't want to give him any ideas.

So, really, based on everything you've said, there is only one way to find out for sure.
posted by thebazilist at 2:36 PM on August 22, 2011

@thebazilist, I would consider myself average. I think she could realistically find me attractive (she has a thing for beards and not-pretty guys; I sport the whiskers and and am definitely not the pretty boy type).
posted by chrisfromthelc at 4:03 PM on August 22, 2011

chrisfromthelc, I say this with all the respect and love in the world: GET OFF OF THE DAMN COMPUTER AND GO PUT THE MOVES ON THIS LADY ALREADY. Seriously, bro. Stop worrying if you're "attractive enough" for her. No one cares! If she likes who you are, she doesn't care either! It's been almost 24 hours since you posted the question and you apparently still haven't talked to her--chopchop!
posted by phunniemee at 4:08 PM on August 22, 2011

@phunniemee: Dude! I'm waiting on her to get back in town from a weekend trip! I'm gonna do this thing in person! I swear!
posted by chrisfromthelc at 4:29 PM on August 22, 2011 [1 favorite]

Hmm...I'll allow it, but I'm keepin' my eye on you, boy. ಠ_ಠ
(I keed, I keed.)

posted by phunniemee at 4:32 PM on August 22, 2011

So how'd it go?
posted by Brandon Blatcher at 7:16 AM on August 24, 2011

Yes, inquiring minds and all that.

Also: I would never spoon or change in front of a guy, all blasé, if I didn't like him.
posted by jlunar at 8:39 PM on August 25, 2011

Come on, man, how'd it go?
posted by athenadanae at 8:52 PM on August 28, 2011 [1 favorite]

I hope the lack of updates mean that everything went well and they are both staring moonily into each other eyes to be too busy writing something on AskMeFi.
posted by moiraine at 3:24 PM on September 1, 2011

For those of you still playing along at was a giant fail. She once again cited the "won't date people she works with" thing, so I told her that the "acting like my girlfriend" thing is something that I only do with girls who are, or want to be, my girlfriend.

We're still friendly and working together, but I've definitely kept things very much platonic and above board. No touching, hand-holding, sleeping in the same bed, etc, etc.

Oh, well. Next, please! I've got a date with a seemingly awesome girl Tuesday night!
posted by chrisfromthelc at 12:21 PM on September 2, 2011

Well, three cheers for being assertive, at least! Have fun on Tuesday, bro.
posted by phunniemee at 12:25 PM on September 2, 2011

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