The dreaded ‘workwith’ induces stomach knots and all sorts of anxiety for most wine sales reps, particularly newbies.

For those of you not in the wine world, workwiths are essentially forced day-long blind dates where you are expected to take a supplier representative from a winery or producer around with you to all your best accounts so they can present their wines and hopefully (fingers crossed) make some sales so they can go home happy.

Should seem harmless enough… until you realize that your “date” for the day will be tagging along with you EVERYWHERE — to lunch, on to a crowded subway, on your midday caffeine hunt in the depths of Queens, while staking out a parking spot after circling the neighborhood for umpteen times, when you have to pee so bad you think you might explode and there’s no bathroom to stop at for at least another twenty minutes. And that they will be traveling with you, in your car, barely a foot away from you, from place to place and through all the standard NYC traffic in between, all day long.

If you’re lucky, the supplier representative will be incredibly affable and you will have a beautiful day! I can confirm without a doubt that this has indeed been known to happen, and more often than not too if you’re at a company that is the right fit for you.

Ideally there will be just enough small chat while you’re trapped in the car to both avoid a 30-minute awkwardly-silent drive to Brooklyn and also to really get to know each other on a surprisingly personal level. Maybe you’ll learn about an interesting new documentary about the Hasidic Jewish population near Williamsburg in Brooklyn, or what a nightshade is and why you should be avoiding them as part of a regular diet, or some new wine-related phrases in Italian from a winery representative. You’ll hear who has been in a band since they were a teenagers and still rocks out at local restaurants with some buddies from time to time, and even issues of race that threatened to tear a family apart when a white wine rep introduced her Mexican boyfriend to her family.

You will dash from account to account amidst the interesting conversation, closing sales with ease simply because the supplier clearly explains why their products make sense for them and their store, without boring the buyers to tears, all while speaking in clear English or the buyers’ native language, which is significantly more ideal. Your buyers at the retail store will love that you brought this lovely supplier rep by and be eternally grateful to have met them, for the stimulating conversation, and for the pleasure of not only tasting but also purchasing their wines. Everyone leaves each account feeling downright elated.

You grab lunch at some point at one of your swanky accounts that is sure to impress them since they always thought of Queens as cheap (read: not Manhattan prices), or at a restaurant with a wine buyer who has been dying to meet this supplier since he loves their wine so much and just wants to talk their ear off over a comped meal, or even at a random restaurant in the middle of Flushing because your supplier has been craving authentic Chinese food and they don’t have any good options in the Florence, Italy area.

At the close of the day you will drop them off at their hotel, which is conveniently located within minutes of your last stop for the day, or at a nearby subway stop that you barely have to travel out of the way to get to. You might even offer to hang out with your newfound suppler friend while they wait for their dinner reservation/have nothing better to do and go to grab one drink but instead you two end up sitting there for hours chatting and laughing with each other at the bar of one of your accounts.

You will reflect on how you learned so much about their wines that selling it should be second nature from now on. You will realize how lucky you feel to have gotten to know this unique and truly special individual, if only for a short period of time, and how this person must have been an angel sent to help you make your placement goal (and thus a hefty bonus) this month.

If workwiths can go that good, just imagine how horrendous they can get.

You can get stuck with a chatterbox with a super thick accent that try as you might you just cannot decipher since your language skills are subpar, leaving you to “mhmm” and “yeah” all day like a lonely parrot with no cracker and not a clue what the conversation is about or if he wants to stop for the bathroom or if he’s sharing some unique insight about the account you just went to.

Or a mute — So you feel pretty uncomfortable trying to start any more conversations that you know won’t go anywhere because you tried to start no less than 12 in the last 30 minutes and they all resulted in a one word grunt. While simultaneously trying not to start unconsciously singing off-key out of boredom to your fire Spotify playlist like you always do when you’re in the car, sitting in traffic, but usually by your lonesome.

Or, just a garden variety arrogant prick who is rude to both you and your buyers. Who doesn’t take his job seriously so it makes you look like a fool in front of your customers for bringing this dumb supplier there. Who makes tone deaf and downright offensive comments to you, about you, about other people that you know and respect in front of you, etc. etc.

Or even a drunk that uses his expense budget as a reason to order two bottles of wine for the two of you at lunch, in the middle of your work day when there are still several important accounts to see that are counting on us to be prompt. When you still have to drive to these other accounts and make it the hour and a half home so you won’t be imbibing along with him, so instead you sit there watching him get sloshed and make a fool of himself in front of the waitstaff solo. And then watch him embarrass himself at your next and now last account visit of the day because he cannot stop slurring.

Or worst yet, you can get stuck with a person that just plain smells bad, after schlepping around all day in the heat and humidity just before a summer downpour. Who smears his sweaty hands all over your nice clean leather seats, and on the entire door, not even just the handle — you can say bye bye to that lovely new car smell after that. Who insists on eating as I drive to the next account, so I end up watching him, out of the corner of my eye, sprinkle crumbs all over my car as he brushes them off of his lap after every bite.

The supplier rep makes or breaks the workwith experience. Some workwith days have literally been the most memorable and exciting of all my days in the wine industry. While others have left me wanting to drink the remainder of the contents of my wine bag (some six plus half-filled wine bottles or so) so I could forget that day ever happened.