Puss In Boots

Hello Ladies, I need some advice...here is my background info: Mid-30s White fella, living in Hayward, WI. I am 6' tall and a thinner than most people in Hayward, but not really saying much...let's go with Husky. I have boyish good looks and a out-going personality. Most of my dating came in my college years at Stout (you know, when in doubt go to Stout!). So, I am very interested in a young lady. I need assistance on asking her out, as it is complicated. "Sally" is a bartender at my regular hangout. I see her at least 5 days a week. We are friends, but I want more. I don't want to make things awkward, but I really want to make my move. However, I don't want to have to change bars either. Please help.

(Also -- in a separate email) Can you please do a breakdown on female grooming or lack thereof and what that says about a lady's crazy factor?

~Johnnyboots69

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In honor of Friday, it's 2-fer-1 day in the Chickadee Lounge -- Mister Persistant (aka, Johnnyboots69), graced us with TWO emails since our grand debut, so I thought we'd tackle them both at once. So, Johnny -- if that is your real name which we seriously doubt -- sit back and enjoy.

A couple of things here-- first of all:

Hayward, really? I have a house in Hayward and am there often. Hey, I'm single, and I dig boyish good looks and outgoing personalities. And, as you know, PBR! I could solve your problem really easily -- fall in love with me instead, and you'll forget all about "Sally."

No, seriously dude? The bartender? Sigh. This is a tough one, because most bartenders are either 1) sluts (male bartenders), or 2) so freaking sick of being asked out that they just want to roll their eyes (female bartenders). That said, you claim that you are already friends, which I'm assuming means that you know each other better than just what your favorite drink is. I would probably straight-up just ask her out. If there is something you know she enjoys (ie, bowling, comedy, live music), ask her if'd she'd like to join you sometime. If it works out, awesome-- not only do you have a new girl, but you just scored free beers for life from your favorite watering hole. If it doesn't, it doesn't-- but nothing ventured nothing gained, right?

But here's where things get tricky -- without conducting a proper SWOT* analysis of this chick, Kat and I don't know what her Crazy Threat Level is -- if she's a nice girl-next-door from Wisco who will be able to maintain her composure and class if not interested -- or if things go south -- I think you're safe and your hangout won't be threatened. We'll call that Crazy Threat Level: white. No harm, no foul. However, if this chick has a potential Crazy Threat Level of bright flaming glow in the dark fuschia, you could be screwed -- if she's the type of bartender-chick that is wasted every weekend, dating lots of customers, and generally has the maturity level of a gnat, then I wouldn't even recommend going down this road -- or be prepared to give up your watering hole forever (or until she gets fired for calling in hungover one too many times).

All in all, if she's the quality chick you think she is, we shouldn't have a problem. Be advised that bartenders get asked out ALL the time-- and usually have a bit of a schtick / riff worked out for when they are not interested. If she's not a quality chick, well... then we question why you want to date her in the first place (actually, we don't question this at all, because for reasons I've previously mentioned, men seem to dig unsuitable women).

NOW! Onto your next question, and I have to admit this puzzles me a bit. I'm not sure what we're talking about here. Are we talking about normal hygiene, like tooth-brushing and hair-washing? High maintenance grooming like manicures, pedicures, and facials? Or are we talking about, ahem, below the belt grooming?

If' we're talking about the basics, I think anything short of Always Being Clean When You Are Around Other People is a bit slovenly -- I'm low / medium maintenance, so I'm never the chick that is perfectly put together at all times, but I am a big fan of showers, clean hair, and fresh breath, so those are "must haves" for me. If I'm going out on a date, you can guarantee I've put quite a bit of effort into my appearance -- I mean, I'll have good hair, a cute outfit, and my socks will even match (and if I think there's a chance of you seeing them, my bra and undies will too). All the spa stuff is personal preference and based on money -- I will say that the higher maintenance a chick is, the more likely there is to be drama. Either because she'll meltdown, or because you will. Some women (like myself) are big into the manicures because I need to have a professional appearance at work (and trust me-- they notice your hands and your shoes. Always). I work out a ton, so massages are almost a necessary luxury. But if you can't handle a chick that drops wads of cash on her own indulgences, then don't try dating her, because I guarantee those habits carry over into other areas of her life.

If we're talking about below the belt grooming here, again -- I'm going to say this is all about personal preference of the woman AND the man she's sleeping with -- and guys, let me be the first to say, some of you have some VERY ODD PREFERENCES. But that's fodder for a future post. Wax it all off? Bushy and beautiful? Landing strip? Everybody's got their preference, but the important thing here is cleanliness -- I think that goes without saying. Also, watching what you eat and drink leading up to moments where you might be, ahem, en flagrante goes a long way (yes, it does make things taste and smell different, for both men AND women -- so guys, eat your wheatgrass and avoid the pickles and coffee. Please).

I think it's safe to say that a woman who has poor hygiene probably also suffers from some serious self-confidence / depression issues, and you should steer clear of that for fear of her going off the deep end.

That's all I got on this one, plus I think my vicodin just kicked in, so I'll hand it back over to the lovely Kat for further commentary.

Sugar and spice,

~Jess

*that's "Strengths, Weaknesses,Opportunities, Threats" for those of you not in the business world.
**Didja see what I did up there with the title? Didja? Didja? I'm pretty proud of this one. Puss -- because he's both scared to ask her out, and the later discussion of personal waxing, and boots because his name is Johnnyboots. I kill me.***

***This might be the vicodin talking.