(Photo credit: Karyn Polewaczyk)

A few weeks ago, I met a group of friends for a movie and cocktails. (We saw the Great Gasby—don't hate.) After closing our tab, we bid our goodbyes and prepared to go our separate ways—but instead of raising my hand for the nearest cab, I opted to walk home to South Boston from Downtown Crossing.

“Are you sure about that?” my friend’s husband asked. “It’s kind of late to be walking by yourself.”

True: it was well past midnight, and a Friday night to boot. But I’d walked home just the night before after a music show in the Theater District, and arrived home sans scratches or scariness—in fact, I’d enjoyed the stroll amidst the vacant city streets. When I proudly offered this information to my friend’s husband, he gave me a skeptical look and insisted I text him when I arrived home so he and my friend knew I made it back okay. (My friends’ husbands are good like that.) I agreed, and went on my way; 45 minutes later, I turned on the light in my small studio apartment, kicked off my boots, and sent a goodnight text to my comrades in the North End.

I wound up walking home the next night (post-party at Revere Hotel’s Space 57), the following Saturday (post-dinner at Silvertone), and last night (after spending some quality time in a hidden cove of the library). I’m not sure if it’s the meditative quality of walking alone, that I’m getting a free workout, or that I’m simply smug about saving on cab fare, but I’m hooked—and with more gorgeous weather (finally) on the way, you can bet I’ll be doing a lot more walking after midnight. If you live within the city limits, I recommend you give it a try, too.

Of course, there are a few things to take into consideration. Like, for example, being relatively sober and aware of your surroundings—that means ditching the earbuds and keeping your gadgets at bay to avoid distraction—and keeping cash on hand for a cab should your safety feel compromised, or if you get lost (be familiar with your route, too—test it out during the day if needed). Wearing comfortable shoes isn’t really an option, it’s a must—I’ve had good luck with my Frye boots and a pair of Gaimo espadrilles (trust me when I say that well-made shoes are worth their weight in gold if you’re a pedestrian by default). And at the risk of sounding cliché, if you’re a woman, it’s in your best interest to take extra precaution. Checking in with friends is a no-brainer; I also recommend taking a basic self-defense class (this one in Charlestown is free and runs almost every Saturday morning) and registering for a pepper spray permit with the police department.

Boston is touted as a walking city, and it’s just as true in the witching hours as it is in broad daylight. All it takes is a little savvy, a swagger in your step, and basic street smarts—plus good friends to keep tabs on your whereabouts.

(Photo credit: Chad Griffith)

Imagine this: it’s Friday night, and you’re out with your friends at a local watering hole. You spot an attractive stranger from across the room, and briefly lock eyes. You report your findings to your group and reach a general consensus: he is, indeed, cute, and you should definitely introduce yourself.

Except, maybe you’re shy. Or maybe you’re not sure if he was looking at you, or if he was looking at the person standing behind you. What if he’s got a girlfriend? And how embarrassed will you feel if you have to slink back to your friends without a digit-clad cocktail napkin in hand? Slowly but surely, the opportunity to say hello passes, and the next day, you kick yourself for holding back.

As I mentioned in last week’s post, there’s a slew of new apps designed to solve the availability equation, where, depending upon which service you choose, you can vet nearby prospects’ interest, and, if it’s mutual connect accordingly. But is that really connecting, or will these programs drive us further apart?

I spoke about the matter with relationship expert and coach, Terri Trespicio. (You may recognize her from the cover of Boston magazine, where she was featured in its Single By Choice article last year.) Connecting with strangers is not just for the brazen, folks. Read on for her tips on how to make approaching strangers easier, and why bouncing back from rejection is part of the (dating) game.

While flipping through the May issue of Marie Claire, I came across a piece called The Insta-Date Explosion, which features a slew of GPS-addled apps designed to assist users in finding dating prospects on-the-go. One device, called—ahem—Bang With Friends, will even help the carnally forlorn uncover potential nearby one-night stands. (No pun intended. Okay, slightly intended.)

Last week, I challenged myself to a weekend on the cheap, where I’d ideally spend no more than $20 each night out. Even though I had well-thought out plans in place that would almost guarantee my ability to stick to my budget, I was nervous: I tend to wax spontaneous, and, admittedly, I have a taste for decadence in small doses that can quickly add up.

I’m pleased to announced that not only did I succeed, I exceeded my own expectations by spending a total of just $49.45 over the course of three days. Of course, a bit of creativity is helpful—as is having friends in the right places—but I’ve proved it’s possible. Here’s how I did it, complete with photographic evidence (compliments of this writer) for inspiration.

(Photo credit: Karyn Polewaczyk)

After spending the entire month of April celebrating my birthday, my wallet has been pleading for a break. But with warmer weather and longer stretches of daylight finally here, the thought of staying in to curl up with a book on a Friday night to save money just doesn’t have the same appeal as it did in, say, January.

And so, I’ve created a challenge for this coming weekend: to go out for less than $20 per night. That figure includes transportation, food and libations, entertainment, and anything else that might pop up between the witching hours of 9 PM and 2 AM.

Of course, it helps that I have a set of loosely-defined plans in place to keep me on course—two art gallery openings and a tequila launch party—but even the most well-thought out plan can take a turn for the unknown, as evidenced by my preference for shiny, bubbly things capped in gold foil.

I’ll report back next week with my findings—and in the meantime, feel free to share your own tips on going out on the cheap in the comments below. Wish me luck, as long as it goes with the boots made for walking I’ll invariably be wearing all weekend to cart myself around sans taxi.