I like the bartender

Thank you to all of you who came out to visit me at Globe Santa at the Pru over the weekend. I'm sorry I wasn't wearing a better outfit. This letter is good for a Monday.
So first of all, thanks for the insight and entertainment; I am impressed by your advice and logical approach. I have only just recently started reading more regularly. I have a lot to learn. On to my question (first one ever!). I am interested in this new bartender at this restaurant/bar that my friends and I go to a good amount. We are kind of a big deal there. Not really. But, I am friends with a few of the other bartenders who work there, mostly girls (never dated/hooked up with any of them). I have only been there a couple times since she has started working and it’s not like we have had a ton of interactions but I was introduced and we have talked a good amount before it gets too busy. She seems smart and has a great personality. Anyways, I don't know if she is interested, has a boyfriend, is actually cool/fun to hang out with (when she isn't looking for tips), etc. My concern is, she is a bartender and I assume she gets hit on all the time/asked out by random drunk dudes while working (is that a wrong assumption?). Also, I think the only place I will see her is this bar. So, how do I separate myself and what is a good approach, as to not come off as a creep/boring? I don't know much about what she likes to do. Should I just ask her to grab a coffee sometime (too boring?). If you were wondering I am 24 and I tend to over-analyze things and be indecisive; trying to work on it. Sorry if this is too long, please edit as you see fit (or in anyway that makes me seem awesome). Thanks for your time and hope you have a great Christmas (or any other holiday you may celebrate this time of year).

– Stuck Between Stations, Boston

SBS, I'm usually opposed to middlemen, but in this case, I think you might want to ask the other bartenders if she’s single, looking to date, etc. You’re right – bartenders get hit on a lot. And they have to be nice because you’re the customer. It’s hard to tell whether bartenders are friends – or if they’re just pouring and listening because they have to. I do think it’s possible for a bartender to fall for a patron. Not probable, but possible. Just consider this – if you go on a few dates with this woman and it doesn't work out, will you be ostracized from your favorite bar? Is it worth getting to know her better before you decide whether she's worth pursuing? If you’re more than sure you want to date her, I’d start by asking your mutual friends if she’s taken. If you can be patient, I’d wait a bit to see if you can get to know her better before you take the next step. After a few more conversations, you’ll either like her more or less – and you’ll be more confident about making a move … or maintaining bartender-customer relations. Readers? Are any of you a bartender? Has anyone dated a bartender? How can he ask her out? Share.

– Meredith