Editor’s note: This is a guest post from Joe Weber of Dappered.com.

‘Cause I don’t care too . . . much for money, money can’t buy me love. —The Beatles

If you’ve decided to take on the challenge of dating women instead of simply hanging out with them, there’s both good news and bad news.

The bad news is that you’re going to have to overcome your nervousness and fear of rejection.

But the good news is that taking women out on dates doesn’t have to be expensive. It simply takes a little more thought.

Too many men make the mistake of believing they can buy their way out of thinking. But creative, cheap dates are often the best kind. They’re more memorable than the standard dinner and a movie, and when a woman sees that you’re thoughtful, she won’t care how much dough you spent on taking her out (if she’s a keeper, that is).

So here are 10 fiscally responsible options for when you’re short on cash but still want to impress her with a terrific date.

1. Wine Tasting

Wineries are sprouting up everywhere this side of Antarctica. Most of these upstarts allow wine tasting for free or for a very small price (and often times, those that charge let you keep the glass.) Go and learn about the different wines, what they pair well with, and keep mental notes on which varietals she enjoys the most. Knowing a woman’s preferred type of wine isn’t as important as knowing her eye color, but it helps. As counter-intuitive as it may feel for those of us who see wasting alcohol as a mortal sin, make sure you use that spit bucket. You’re driving, you need to be responsible, and if you swallow every taste you’re not going to be fit to drive her home. You don’t have to spit every taste, but showcase some restraint. She’ll notice and appreciate it.

2. Hit a Flea Market

Unlike antique shops, flea markets seem geared for the young and not as affluent. The merchandise is almost always more interesting if not downright weird. Same goes for the people in attendance and those who are selling the goods. You can watch people barter, look over pieces of furniture that are probably haunted, and maybe pick up some small gift for your date if something inexpensive catches her eye. If it’s jewelry? Who knows. Maybe it won’t even turn her skin green. (Or it could end up being some awesome treasure.) Try and stick to outdoor flea markets that have a good reputation. Not those once in a blue moon indoor sales which charge you an arm and a leg before you even get to lay eyes on what’s for sale.

3. The Sunset Hike

Going for a meandering walk with no real destination can be fun, but hiking to the top of an easy to get to peak to watch the sun go down gives you purpose. Keep it to under 45 minutes. You don’t want to go on some epic journey only to end up stumbling through the dark. Reward yourselves with a beer or glass of wine afterwards at a cozy pub. This works terrific in the fall when you can see all the changing leaves around you.

4. The Photography-Filled Afternoon

File this one under the category of two-birds/one stone. Most of us have relatives in other parts of the country (or world) and you never know what to get them for their birthday or the holidays. Go on a photo hunting expedition in your hometown for the places and scenes that best represent where you live. When you’re all done, pick 12 of the best and hit one of the many websites that allow you to upload photos and create wall calendars. There’s your gift for Grandma and Grandpa who live a few time zones away and would love a reminder of what it looks like where you live.

5. The Bicycle Picnic

Picnics are always at the top of everyone’s list for cheap and romantic dates. But mixing in a leisurely long bike ride can make a nice difference. It’s relaxing, you get to enjoy some scenery on the way, and it’s far more romantic and engaging when compared to fighting through traffic and finding a place to park. Keep the menu simple, know any open container laws that might apply to your eventual picnic destination, and make sure you’ve got a backpack and bike gear rack that can handle your load. Take a bike lock with you. You might end up taking a detour on the way home for ice cream.

6. Take a Historical Walking Tour of Your Town

Almost always free, historical walking tours actually make you stop and appreciate the history that most of us drive by every single day. We’ve got our own point As and point Bs, and most of us rarely spend time focusing on the places in-between. Usually these tours are led by volunteers who can be real characters, and the buildings and their stories are never boring. Both (the guides and history) will provide for plenty of conversation at the cafe or bar afterward. Nostalgia, history, architecture, an appreciation for the past… it’s all wrapped up in one of these on-foot freebies.

7. Cheering on Your Local Roller Derby Girls

For the cost of one cheap seat at most major league games, you and your date could watch one of the hundreds of local roller derby clubs duke it out with a rival. Usually a ticket will let you see a couple of bouts, and the speed and spills are the real deal. It’s something different but still sports related, with just enough adrenaline, which doesn’t involve sweaty guys for once.

8. The Untraditional Movie Night

There are two options here. First, if you’ve just jumped into a relationship, skip the new romantic comedy that just hit the Redbox, and instead go with a classic like Casablanca, To Catch a Thief, or even the goofy-as-all-get-out original Ocean’s 11. Grab some takeout, make a meal, or have some cocktails on hand that line up with the plot or location of your chosen old Hollywood story. Set an upscale mood by dressing up a bit. You don’t want to look like you’re settling in for a night on the couch because you have the flu. Just because you’re at home watching a movie, doesn’t mean you shouldn’t dress up for her.

For those that have been in a relationship for awhile, consider reenacting your first movie date. We all (should) know the first movie we saw with our significant other. Find it for cheap on DVD, grab a wicker type basket from a craft store, dress it up with some tissue paper, and load it up with popcorn, M&Ms, and other movie theater-type snacks. Deliver it to her and ask her over for a movie night. Should cost you less than the arm and a leg you spent on just the popcorn and sodas alone when you two first saw it in the theater.

9. Farmer’s Market in the Morning, Making Dinner Together That Evening

Staying in and making dinner together is as romantic as it gets, but use your dinner date as an excuse to hit your local farmer’s market that morning. Stroll past the different vendors, and eventually you’ll start assembling a pile of fresh local ingredients that you can use that evening. You don’t have to get everything at the market. Maybe just the foundational items for each course–perhaps a couple bunches of kale to saute up with some olive oil and garlic, a couple of local organic chicken breasts that will be plenty easy to stuff, and some berries to pair up with shortcake for dessert. Get creative, then use the middle of the day to find some easy recipes and pick up the rest of the ingredients you’ll need.

10. Monopoly. Loser Buys Dinner or Drinks

Don’t scoff at board games (or cards). They can make for a terrific evening in (if that’s what you’re looking for). Put a friendly couples related wager down on the outcome (dinner, drinks… I’m sure your imagination is wandering to other places). It’ll make the game all the more interesting. Skip Scrabble or Trivial Pursuit. Those can get too mentally competitive. Monopoly has enough chance involved that no one’s feelings will get hurt (yours included) if someone completely dominates the other. And dominate Monopoly you will if you nab those orange properties (it’s true, they’ve done studies). Win, and if the prize includes a night out on her dime? Then this cheap date idea just produced another. Well… for you at least.

What are your favorite cheap date ideas? Share them with us and if we get some good ones, we’ll do another installment.

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Joe Weber is the Director and Editor of www.Dappered.com where affordable style is the one and only focus. He believes that living right, living well, and looking good doesn’t mean you should go broke in the process.

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