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My Week Of Flirting With Women


Wondering where to meet women now that you’re single again? Here, one forty-something writer shares his week-long flirting diary with us — and where he had the most luck with the ladies.

By David Bakke

t has now been about one year since my divorce, and during that time, I’ve had varying degrees of luck with online dating. In order to increase my success, I decided to try a different approach. I devoted an entire week to the singular goal of getting a date out in the real world — the old-fashioned way. My
I specifically targeted women who I thought would be a good fit for me.
week-long dating experiment recently concluded, and while I am pretty exhausted and my wallet is a little lighter, it was an eye-opening and rather successful experiment.

Here’s how my week went, broken down on a day-by-day basis.

Monday: Gym
On Monday, I actually hit the gym twice (first at 7:30 a.m., then later at 6:30 p.m.) to improve my chances. Either way, it’s a tough nut to crack with so many people listening to digital music players and focusing on their workouts.

In my morning session, I specifically targeted women who I thought would be a good fit for me. I am in shape, but by no means am I a fitness buff. I saw my best opportunity in the free weights section, where a woman approximately in her mid-thirties caught my eye. I struck up a conversation as she completed one of her sets and asked if I could use the weights while she rested. We exchanged a bit of small talk; however, I didn’t sense much return interest, so I simply moved on. I didn’t approach any other women that morning.

In the evening, I attended a co-ed step class, which provided some intense exercise — and also great prospects, as there were only three other guys in the class and 18 women. I couldn’t strike up any conversations until the class finished, though at its conclusion, I had a nice chat with an attractive woman in her forties. Although I didn’t get her phone number, she asked if I would be returning the following week — and her body language was encouraging. I told her I would, so that made the outing a success in my book.

Takeaway lesson: I wouldn’t expect much success when trying to meet women at the gym. The majority of people there are simply focused on their workout. In fact, a recent Happen magazine survey reported that 63% of women said the gym was the absolute worst place for men to hit on them. Yikes! But if you’re up for a challenge, keep your approach low-key and don’t come off as though you’re looking for a date — even though you are.

Tuesday: Grocery store
I visited my grocery store around 6 p.m. because I knew it would be filled with after-work shoppers. And since I’m a vegetarian, I picked this section of the store in which to focus my search. Before long, I found a prime target — a single mother who had a small child with her. I picked up some organic pasta and asked her if she’d ever tried it. She said that she had. Bingo! We talked for about 10 minutes, discussing the benefits of organics, and I asked her if she’d like to get a cup of coffee sometime. She said yes. Jackpot! We exchanged phone numbers and met for lunch later that week. It went really well, and we’ve made plans for another date.

Takeaway lesson: Your odds of finding love in the grocery aisles are better than trying to meet someone in the weight room because there’s no loud music to talk over (or other major distractions, like interacting with a personal trainer). Plus, grocery shopping is an activity where women typically won’t be irritated when they’re approached. Just make sure to “shop” during peak hours to improve your chances.

Wednesday: Art museum
A museum offers a more eclectic, cerebral gathering of people — a great place to go if you’re looking for the “artsy,” creative type to date. Just be prepared to speak intelligently about the artwork on display, or you’ll look foolish.

During my visit, I found many women who seemed like possible candidates. My approach was rather passive: I stood in front of a painting for several minutes until someone came by. I’d make an innocent remark about the work while the person was within earshot, then transition the conversation so that it became more personal. Unfortunately, several attempts at making small talk this way didn’t get me very far. This particular afternoon turned out to be a bust.

Takeaway lesson: Although I didn’t have much luck, I still recommend putting art museums high on your list if you want to meet women. Unless it was just a coincidence, many single ladies appear to frequent art museums and galleries.

Thursday: Coffee shop
Of course, I made Starbucks the venue — they’re just too popular to go anywhere else. I actually visited two different locations, because at the first stop, once I purchased my coffee and sat down, I immediately felt awkward approaching anyone. Most
I managed to get her phone number and called her the next afternoon.
women had books or laptops open in front of them, and I didn’t see a single opening for myself to start flirting with anyone.

I decided then that my best bet would be to strike up a conversation while I was still in line or getting sugar for my coffee, so I moved on to my second Starbucks of the day. My new technique worked much better. I started a conversation by asking an outgoing, approachable, middle-aged woman: “What are you drinking?” She turned out to be the chatty sort, which made it easy for me. We moved to a table with our drinks and had a very relaxed, enjoyable talk. Just when I was about to ask for another meeting, she revealed: “My boyfriend’s out of town, and I’m just killing time until he gets back.” I tried to hide my irritation, politely backed off, finished my cup of coffee, and ended the evening.

Takeaway lesson: Don’t mistake someone who’s “outgoing and approachable” for “single and available.” And if this happens to you, don’t be rude — it makes for bad dating karma.

Friday (early evening): Music festival
I started my Friday evening at a jazz festival. It was a cozy setting, with about 600 people in attendance. I had a blanket to sit on and brought a picnic basket with some cheese, crackers, and wine. I had to move several times before I located some women whom I wished to get to know.

I eventually sat next to two women who looked like they were having a great time together. Even better, they started talking to me by saying that they were surprised to see that my basket didn’t contain beer and nachos. For this, I gave myself a mental pat on the back. I had made a conscious decision to bring the wine and cheese to make myself more appealing to women, and it worked. The music was enjoyable, and both women were friendly. I began to focus my attention on the woman who was more my type; luckily, her friend seemed to respectfully let us have our conversation without interrupting. I managed to get her phone number and called her the next afternoon.

Takeaway lesson: It’s important to consider the image you present to the women you’re trying to attract, and packing the wine and cheese definitely helped me out in this instance. I suppose these two women were accustomed to beer-guzzling football fanatics, and became immediately intrigued by someone who didn’t fit that stereotypical persona.

Friday (late night): Nightclub
I left as the festival was finishing up and walked to a local nightclub. It was nearly 11 p.m. by then, and the place was pretty packed. Among the crowd, I saw a woman whom I recognized from the festival. This made it very easy for me to initiate a conversation.

She immediately asked who the two women were that I’d been speaking with earlier that night. This was a good sign to me, as it showed a bit of interest — and a hint of jealousy. I told her they were just some people I randomly sat beside and talked to during the festival, obviously not mentioning anything about the phone number in my pocket. The conversation flowed easily as the wine I’d imbibed decreased my inhibitions. After talking for nearly an hour, I suggested we exchange phone numbers, which netted me my second success of the evening.

Takeaway lesson: If “nightlife” will be the main way you choose to meet women, time your visit so you’ll arrive when those venues are nearly full. Going to an empty spot at 7 p.m. is simply a waste of your time and money. Also, avoid places with live music, as it’s just too hard to talk over the ruckus.

Saturday: A friend’s party
A buddy of mine whom I hadn’t seen in a while invited me to a party he was hosting that weekend. I thought it would be a good idea, but it turned out to be an unmitigated disaster.

My buddy had apparently informed most of the females attending his shindig that I was moving on from my divorce — and that I was lonely. It was about the last thing I needed, honestly. Most of the women I spoke with seemed more intent on cheering me up than actually conversing with me in-depth. I’m sure I was viewed by them as being “on the rebound,” and therefore, had virtually no shot with getting to know anyone who was single. I was annoyed with my friend, though I know he was just trying to help me out.

Takeaway lesson: If you’re looking to meet women at a mutual friend’s party, avoid broadcasting anything that may put you in a negative light, such as a recent divorce or lost job. It can really kill your chances. However, 50% of women in a recent Happen magazine survey said that a party was the best place for men to flirt with them, so play it smart, guys, and it could be your best bet for meeting dates.

Sunday: Church
I rounded out my week by attending church services. There are not too many attached women who go to church alone, so that makes locating single women quite easy. And, of course, if you’re interested in a woman who shares your beliefs, you’ll have a greater chance of meeting her at church.

The church provided doughnuts and coffee in the foyer after service was over, and I hung out there for a good hour so I could speak with three different women. We discussed the sermon and shared a few personal details with each other. All three asked me if I would be back next week, and I told them that it was likely I’d return.

Takeaway lesson: If sharing a religion is high on your list of must-haves for a partner, this is the perfect place to go. The environment is low-key, and there certainly is no guessing game regarding when someone will be back — unlike health clubs, shops or bars.

Final thoughts
One thing I can tell you about meeting dates is that success breeds confidence. Since I had good luck scoring phone numbers early in the week, I had an easier time approaching women later on.

You may feel most comfortable with online dating — and though it is a great option, try combining it with some real-world interaction, too. It helps you stay socially active, and often, it can net valuable results — you may be surprised. Throughout the week, I only spent about $90, excluding the items I would have purchased anyway. I spoke with 12 women, got three phone numbers, and had one actual date. Not too bad for one week back in the game!

For a woman’s take on the week-long flirting experience, read My Week Of Flirting With Men.


David Bakke is a forty-something guy who recently got divorced and is looking to move on. He writes about managing money, saving on life’s many expenses, and dealing with relationships online at the Money Crashers Personal Finance blog.
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