Relationship Woes and Advice XXVIII: Happy and Perfect!

[Aedilred]

Losing your job over it, per se, is very unlikely unless your workplace has very strict and blanket no-dating rules. Which are, honestly, ridiculous.

Yes, it could cause a HR nightmare if she decides she's going to make a real thing out of it but that also seems very unlikely. Job security is not a factor I would be worried about; you will know better than us if this is likely to be something to cause serious concern.

While I do understand and have in the past agreed with the policy of keeping work and social life separate, I am increasingly coming to appreciate that this is a luxury, predominantly available to the young, and may actually be counterproductive. While becoming best mates with people you have to manage is fraught with difficulty and may be best avoided, the fact is you spend the majority of your waking hours around your colleagues and if you get on well with them, putting up barriers in order to stop yourself becoming friends with them on a point of arbitrary principle doesn't make a lot of sense. Depending on the job's hours and your extracurricular commitments it can be very difficult to maintain much of a social life outside work - and that's assuming you even have one to maintain. And if you're working with friends or your partner then it means you get to spend more time with them.

If you're in a town where you have lots of friends from school or university still around, then it's relatively easy to keep friends as a strictly out-of-work thing, because out-of-work friends are not in short supply. If not, work is actually by far your best opportunity to meet new people. And when it comes to romantic partners in particular I'm generally of the view that if you meet someone you like personally and find attractive, it'd be foolish to pass that opportunity up in favour of any number of internet dates with people you know less well.

However it is still something to be approached with caution, because it's harder to make a graceful exit if she turns you down (or if things fall apart after initial success) and because even in a best-case scenario your workplace will never be quite the same again (which, admittedly, might be a good thing). This makes the gauging of her opinion of you more important than it might otherwise be, but unfortunately there's no easy way around that. There are a few obvious things that it might be worth checking if at all possible (that she's single, that she's not gay, that she isn't a member of a community that wouldn't allow her to date you, etc.) just to minimise the possibility of embarrassment. But otherwise it's a question I guess of making the judgment over whether you like her enough to deal with the ensuing complications (moderated by other factors like how confident you are that she likes you, whether romantically or personally, that she's decent enough not to make your life difficult if she's not interested etc.). Unfortunately that's not a decision we can really assist with I think.