Some advice to the single men of Portland: for your love life and your wallet

So it’s Friday night and you’re at the Old Port. Again. You’re out with your boys, you’ve got your dark “nice” jeans on, that button-up shirt with the vertical stripes, and you’re feeling pretty darn good. And even though you shaved yesterday (girls love that five o’clock shadow), you put on some of that L’Oreal aftershave so you know you smell nice; you don’t wear cologne anymore after your last girlfriend told you it reminded her of an eighth grade dance. It’s getting later and though you came out to meet some women, you have yet to leave your all-male group. A couple drinks, then a few more, still more, and suddenly you’re feeling great. You’re about to order that last beer and then you spot her. She’s at the other end of the bar (they’re always at the other end, aren’t they?) and she is hot. You think maybe she’s stealing some glances your way, and you order your beer with confidence. As you take that first sip, you let your eyes slowly lower to hers. While you lock in the penetrating eye contact, you casually show off your swagger as you cascade to her end of the bar. If you’re lucky…hell, if she’s lucky…she’ll be in a cab on her way back to your place in twenty minutes.

Stop.

While this perhaps seems like an excellent Friday evening, and an even better set up for the early morning hours of Saturday morning, this could be yet another terrible misjudgment of a string of misjudgments by your drunken alter ego. Let me just inform you that as a young twenty-something female, I’ve seen you do this before. And while you think you’re the Casanova of Gritty’s, you actually look like a red-faced, cross-eyed lunatic charging at this poor young woman from across the bar. And that’s the best case scenario. A worse case would be that this “hot” female you’re about to prey upon could actually look as pathetic and googley eyed as you, despite her drunk mind’s opinion on the matter. Let’s say this girl is the Cookie Monster-eyed female equivalent of your intoxicated self. She may not mind waking up to the framed and mounted plaques of your high school accomplishments in the small fake wood paneled bedroom of your parents’ basement. Heck, she even may not be horrified at the idea of doing the walk of shame in front of your Mom’s Saturday morning book club, all the while wearing last night’s tights with runs in them and your oversized University of Maine club softball t-shirt.  Even more, she may not even notice that surprised look on your face in the morning, suggesting that you either don’t remember last night, or were suffering from a case of severe “beer goggles” and wish you couldn’t remember. But, does this really sound like the excellent time you had mapped out in your head?

And hey, if what I’ve just described sounds like a pretty awesome Friday night to you, then disregard the rest of this entry. To each his own, right? This sage wisdom I am about to impart is for those looking for second dates, relationships, or something aside from waking up with a wicked case of morning breath and dizzying regret. Also, for the record I want it stated that I am no prude; I’m all about single people enjoying themselves and having fun. But “having fun” sometimes translates into boring conversations and false alcohol-induced connections. As someone getting pretty tired of the routine come-ons the Old Port has to offer (and that goes for most of my female friends as well), I just figured I’d offer up my own advice for guys who want to meet women they either don’t lament inviting home or might even just call sometime to see if they want to get together again. So, if the secret to meeting a fun, interesting, sexy young woman is not (at least not usually) hitting on every young piece of tail in the Old Port until someone responds positively, then what is it? Well hey, I don’t claim to have the answers to everything, but I do have some pretty good starting points for ideas.

Try approaching a girl somewhere aside from a bar. Like where, you ask?  What do you like to do in your spare time? If you’re one of those adventurous types, try asking the cute girl out at the rock gym. More into books than physical activity? That’s fine, too. Next time you’re perusing your favorite local book store, keep your eyes alert for anyone that strikes your fancy. Meeting someone in a place which suits your interest boosts the likelihood of that being her interest as well. Maybe not. Maybe she hates reading and is only at the book store to buy something for her nerdy little brother’s birthday. But at least you’ll score points for the courage it takes to approach someone.

But maybe you don’t find yourself having a lot of spare time to pursue your hobbies and interests. So what then? All your friends go to the Old Port almost every weekend and you don’t really want to sit at home come Friday just because you didn’t have anywhere cool you like to go during the week that may lead you to bump into attractive women. Well, everyone goes to the grocery store, right? Reaching for the same pasta sauce could be your in. Strike up a conversation while waiting in line at the deli counter.

And look, I’m not totally unrealistic. People go to bars and people meet each other at bars. Especially young people in Portland. However, if you are looking for something more than the drunken one-night-deal, I suggest speaking to a woman earlier in the night rather than later. Say, during happy hour, before things get sloppy downtown. Also, if someone does catch your eye and you do find the stones to approach them, don’t just ask if you can buy them a drink. Introduce yourself and ask for her number. Then do something really crazy. Don’t text her. Call her sometime. Crazier still, when you do call, ask her out on a real date that doesn’t only involve a bar. I know, I know, I must be nuts, but it might actually impress her to see that you want to do something with her besides get drunk (oh, and that other thing…)

So now that we’ve figured out how and where you might approach her, things are looking up. Except wait, oh no. We’ve forgotten something huge. Where the hell do you take her on this proposed date? You live at home because you’re swimming in college debt, or maybe you’ve got your own place but your stupid entry level job pays crap and most of your money goes to rent. So not only are you lacking in ideas as to where to take her, but your wallet’s feeling pretty light these days. Well, have no fear gentlemen because I’ve got some great and cheap suggestions for interesting and memorable dates.

1)      Want to impress her with your knowledge of Portland’s jazz scene, all the while enjoying a great burger for under ten bucks? Kill two birds with one bill at The Dogfish Bar and Grill’s Free Street location. While the blackboard specials might scare away the thrifty diner, the regular menu features burgers and sandwiches for completely reasonable prices. Enjoy your blue cheese burger or your tomato pesto mozzarella baguette while accompanied by the FREE musical stylings of their Friday night jazz artist. Dinner and a show for a very affordable package! Also, if you or your date is into art, this restaurant is definitely the place to eat. The Dogfish has a wonderful reputation as a big supporter of the arts and they boast an array of local artwork (usually for sale) hanging on their walls. Even if you’re not looking to buy any new art (which let’s face it, you’re not because you’re currently scouring this blog for cheap date ideas) it’s always entertaining to check out the often funky and colorful displays.

2)      Show off your skating skills at Portland Ice Arena’s Public Skate-Ok, so I am already envisioning many of my male friends scoffing at this one. But for perhaps the more romantic of Portland gentlemen out there, this is a nice cheap way to get out and do something active on your date in the all-too-long Maine winter. It’s only $5 to skate and $2 for skate rentals. Plus, it’ll bring you back to the old couples’ skate days of a fifth grade birthday party at Happy Wheels. PIA is open to Public Skate almost every day. For a full schedule visit http://www.portlandicearena.com/publicskating.pdf

3)      Reveal your artsy side with a walk through the Portland Museum of Art-On the fourth Friday of every month the museum is free to the public from 5-8 p.m. Even if you don’t know much about art it’s a cool place to walk around and check things out. It is also a great way to start a conversation with your date. Maybe you’ll find you really like the exhibition and you can bond over the unusual technique of Katsushika Hokusai. Maybe you’ll both hate it but at least it will give you something funny to laugh about. Plus, it’s free, so no harm, no foul.

4)      Literary Type? Struggling writer? Bring her on over to Blue on the second Tuesday of every month for Port Veritas’ Second Tuesday Poetry Slam. It’s free admission and they’ve got a wide variety of teas, Coffee by Design, and beer so you can sip on your favorite beverage while you listen to some of Portland’s emerging poets. It's right on Congress Street so if you decide poetry isn't for you or your date, you've got an array of other choices just a stone's throw away. Plus, if you’re feeling hungry, they’ve got an eclectic menu from grape leaves to ravioli. And even better, everything on their menu is under $11!

5)      You got a C in high school Art Fundamentals, the last book you read willingly was “Goodnight Moon” in 1990, and you’d rather eat a bucket of larva than be seen on ice skates by your date. Well, alright. You’re a tough customer but I’ve got one last cheap date suggestion to run by you:  Dinner and a movie. Not very original, I know. However, while Portland’s Nickelodeon Theater may not boast the 15-theater overload the megaplexes at the mall are known for, it’s quite a charming little place. There’s no 3-D at this small 6-screen theater. Just quality movies and…wait for it…cheap ticket prices! On Bargain Tuesdays they offer 5 dollar tickets. 5 dollars! In 2011? That’s unheard of! Plus, located at 1 Temple Street, it’s right in the heart of Portland. After the flick, walk on down to Pai Men Miyake (located at 188 State Street), Portland’s newest Japanese noodle bar. Discuss the movie over $1 Naragansetts and $3 Hot Sake Carafes (Monday-Wednesday after 8 p.m.). The pork buns are amazing and their new spicy miso gives the noodles a healthy kick. For those of you familiar with Masa Miyake’s first Portland restaurant Miyake, you might be pleased to hear the spicy crunchy roll has found its permanent home at this second culinary endeavor. And last, but certainly not least, all the food on the regular menu is priced at $11 or less!

So, as this entry comes to a close, I hope those of you who stuck around until the end will heed my advice. Dating needs to make a comeback among twenty-somethings, and in a big way. The same old Old Port song and dance is so stale it’s beginning to mold. And I get it. Sometimes dating seems like an expensive alternative to the much easier “Wanna come home?” approach that often occurs in what my male friends refer to as the “five minute shuffle” between last call and cab rides home. However, as evidenced in this entry, Portland has a multitude of interesting things to do that will not only impress your new lady friend, but also your accountant. Well, if you had enough money to afford an accountant you might not be reading this blog, but you know what I mean. Until next time, good luck, have fun, spend less, be safe.