9.5 min readBy Published On: February 27th, 2015Categories: Arts and Entertainment, Lifestyle0 Comments on First Date Ideas to Wow Every Type of Woman

Written by Tara M. Kerrigan

You know what I love about a guy taking me to play pool on a first date? Nothing. While I enjoy billiards and beer as much as the next gal, I can’t have any fun now, because I’m too busy obsessing over how uninventive and predictable this date idea was, and how our tongues shall never twine. There’s a reason it’s the first date scene in just about every romance movie ever made – because it’s cliche. With winter’s end in sight, use this great city of ours as your ally: Boston, a city rich in culture, fine cuisine and thanks to its history – unique attractions. Do keep in mind what type of woman you’re aiming to impress, and then, just when you think you’ve got it down – switch it up.
The Tomboy:
Let me guess, the first thought that pops to mind is a Pats, Bruins or Sox game. Great idea. You can sit on your rump inhaling hot dogs, while you watch your date eyeball a pack of sexy, sweaty, athletic, dudes (who aren’t you). Consider getting a little physical with your Tomboy instead, and I’m not suggesting she should open the door to find your pants at your ankles.
Nice day? Take her to the driving range. Granite Links in Quincy is a great spot to practice her swing, complete with the “Snack Shack” where you can grab some causal fare and cocktails. This open patio overlooking the picturesque Blue Hills seems plucked from another space and time, especially on weekends when there’s live music and a raw oyster bar. For something a bit more novel, introduce her to bocce ball. Overlooking the Boston Harbor are the Commercial Street Courts in the famous North End where you’ll mingle with seasoned die hard bocce enthusiasts straight from Italy, (and just when you think you’re in Naples, look up and soak in the view of Old Ironsides and the Bunker Hill Monument to keep you grounded). Rainy day? Skip the bowling and suggest indoor rock climbing instead (check out the brand new Rock Spot Climbing location on Old Colony Ave. in South Boston). Or if she’s adventurous enough to take a shot in the face, indoor paintball is one of the best dates I’ve ever had. Try Boston Paintball in Chelsea.  Any day! Take her to the firing range. You’d be surprised at how many women are secretly dying to shoot a gun. Seriously. For indoor you’ll likely have to trek out to Original Bobs in Salisbury, but on a nice day, definitely try skeet shooting (there are fifty plus shooting ranges spanning MA, find the one nearest you at www.claytargetsonline.com). Now here comes the switch hitter. Once you’ve appealed to her boyish side, do something unexpectedly feminine. Escort her to Temple Bar in Cambridge and order the gooey cheese fondue appetizer with the Basilisk cocktail (trust me), followed by the rich dark chocolate fondue dessert (accented with berries, cake, and maple singed marshmallow). Because after all, she’s still a woman, and the only thing women like more than cheese? Chocolate. Boom.

The Intellectual:
This is a lady who needs to unwind, and you’re just the gent to help her do that. Take her to Laugh Boston comedy club for some nibbles and giggles, or create your own comedy as you trip over each other’s ankles during Salsa lessons (try “Dance in Boston” over in Brookline). If she’s the Type-A kind of lady who simply cannot turn off her brain, then switch it up and bond over a unique game called Geocaching. It’s a real (outdoor) treasure hunt involving a GPS enabled device (a GPS enabled mobile phone will do). Participants navigate to a specific coordinate, find a hidden treasure, then replace the treasure with an object of equal or greater value. Shop for the cache together first at one of the quaint antique stores on the stony sidewalks of romantic Charles Street. Then, to plan your adventure, go to (www.geocaching.com) to discover one of over 200 geocaches in and around Boston. Now, if you truly want to blow this special lady’s mind, (and your budget permits), reserve a table at a restaurant that dabbles in molecular gastronomy. Molecular cuisine uses avant-garde cooking techniques and equipment to create mind twisting, conversation provoking dishes to delight her palate as well as her cerebellum. If she’s serious about food, Clio is an absolute must, or visit the Liquid Art House, (which doubles as an art gallery), for aesthetically stunning edible masterpieces. For a real life Jetsons experience, launch over to Cafe Art Science in Kendall Square. While their savory is only slightly scientifically influenced, request seats at the bar for a sumptuous supper and some seriously satiating sci-fi spirits. Say that tongue twister after a few of their vapor essenced, burnt citrus concoctions complete with drill holed ice cubes.
The Sophisticate:

Unlike the malleable intellectual type, the sophisticate doesn’t mess around. She know precisely what she likes – the finer things. Think Opera House tickets and Michelin star priced dining, and watch your wallet shudder. To impress the sophisticate without having to sell your car you’ll need to be resourceful. Start by going to www.localwineevents.com and search in Boston for a vast list of wine and food related events all over town. You’ll find everything from pricey elaborate wine pairing dinners at the Gaslight Brasserie, to affordable bread making classes at the Boston Center for Adult Education, (and everything in between). Hotels such as the Charlesmark often host affordable tasting nights, and don’t forget about our very own Boston Winery here in Dorchester. If wine simply sours your puss, visit Harpoon Brewery or Sam Adams for a beer tour, or for fine spirits head to the Bully Boy Distillery. Now that you’ve got the edibles in order, try to switch it up and draw out her artistic side. Hit the Urban Art Bar in South Boston for a little paint and sip, where you’ll create genuine works of art, side by side and imbibe (and hey, she’ll have a keepsake to remind her of your fabulous first date). Keep an eye out for Groupon or Living Social offers for all of the above, a great way to skirt around cost because you’re not made of money, right? Oh you are? Call me.

A word of caution: if you go the coupon route choose only the events that you can book online, in advance, and use your coupon on the down low. You don’t want to be busting out that bad puppy in the middle of a date with your fancy lady friend.
The Artist:
The artist loves all things culture, so this should be an easy one. For something traditional, a trip to the Museum of Fine Arts museum is always nice, but even nicer when there’s a specifically planned agenda by thoughtful and considerate you. Research current exhibits and be sure and tell her why you chose the one you did with her in mind. Reserve a table for after at Bravo restaurant on location to dine and discuss the pieces (since art is subjective, you need not be a connoisseur). Or if you’re into architecture, visit the visually exquisite Isabella Stewart Gardner Museum (the courtyard is a work of art in and of itself). The Gardner also hosts intimate concerts periodically (check their site for a calendar of events). For something a little less orthodox and ripe with comedy, check out MOBA (the Museum of Bad Art). It is, precisely what it sounds like. But if museums in general bore you to tears, no need to force it. Any type of performance arts, (especially outdoor theatre, ie. Shakespeare on the Common) will sing to an artist’s soul, and when all else fails; live music. If concert tickets are not in your budget, there are frequent free concerts at the Hatch Shell on the Esplanade. Check your local bars, pubs, restaurants, and even coffee houses to see which offer live performances, and not strictly musical in nature. For example, Savin Bar & Kitchen in Dorchester hosts open mic night for aspiring artists where you can enjoy free poetry while indulging in a scrumptious yet affordable meal (order the Wood Grilled Teriyaki Salmon. For the price: Mind = blown). For a full listing of venues in your area visit www.openmikes.org. If this all sounds too reflective, switch it up and consider something breezy and upbeat like a Jazz brunch at Beehive in the South End.
The Hippie:
She’d likely prefer the word humanitarian over hippie, (mental note) but however you classify her, the world is your oyster when it comes to dating this open minded, open hearted, free spirit. Appeal to her compassionate side, by volunteering together at a local homeless shelter such as the Pine Street Inn, or your town’s local retirement home. If the idea consorting with the homeless (or the elderly) for the day makes your skin crawl, keep that filthy little secret to yourself and set your sights to nature. As one with mother earth, the hippie loves anything to do with the great outdoors. You may want to avoid the obvious Boston attractions such as the Freedom Trail, and seek out lesser known gems like the Boston Harbor Islands. A quick ferry ride will whisk you to unique events, as in a clambake on Spectacle Island or a haunted walking tour of George’s Island. If you’re lacking in the sea leg department, a bike ride, a picnic, or even better – a bike ride to a picnic are simple, yet sweet, ideas. With the money you saved on a restaurant bill, rent a couple Hubway bikes, then hit up American Provisions gourmet shop in Southie to stock up on meats, cheeses, premade salads and unique chocolates. Then get those gams going down to Castle Island where you’ll plop down at the feet of Fort Independence, and dazzle your date with historic tales of the fort’s most famous guest, Edgar Allen Poe. (The famous Cask of Amontillado is said to have been authored by Poe based on actual events at the fort). Or to switch things up, let your nurturing side shine. Start by taking her to the South Boston Farmers Market on 446 W. Broadway and allow your date to choose a set number of ingredients from their vast array of fresh, locally sourced goods. Then head to either abode for a quick fire challenge, where you’ll amaze her by inventing a delicious meal from her chosen fare. If you’re no Gordon Ramsey, you can always try a one time cooking class together. Flour Bakery in the Fort Point District has some fun classes lined up for the eagerly anticipated Spring (inquire at [email protected]).
Whether you’re new to Boston, or born and bred, be sure to brush up on the current local happenings. While some landmarks may never falter (hang in there Green Monster), restaurants and businesses are changing as quickly as our neighborhoods themselves. Above all, have fun. While the objective may be to impress your date with something authentically Boston, really the ultimate goal here is to get to know one another in an environment that is enjoyable, and memorable, for both of you. Oh and to score that second date.