Back in May, my buddy Saving Mentor posted a fantastic “heads up” post on the Aeroplan Star Challenge, where you could earn 16,500 points basically free.

For those of you who aren’t familiar with Aeroplan, they are a points program where you can get free flights for Air Canada as long as you have a minimum number of points. You can also get merchandise or other paraphernalia, but I would much rather get flights.

16,500 points is the typical number of points you would get if you signed up for a Aeroplan credit card, usually with an annual fee (e.g. $129 per year for an Aeroplan points card). 16,500 points gets you a free return short haul flight. If you have 25,000 Aeroplan points, you can go anywhere in North America on Aeroplan!

The task to get the Aeroplan points was to collect 70 points. One of the easiest ways to do this was to go to Esso (a participating Aeroplan partner in the challenge). Each transaction is worth 2 points. Therefore, if I got 35 transactions in the specified time period (28 days), I would have reached the 70 points, and thus the 16,500 Aeroplan points.

Of course, this got me excited.

You’re probably wondering… how does one get 35 transactions with Esso? Well, not through $45 fill ups at the gas station. If I only fill up every 10 days on average, that’s a measly 6 points. Not enough to score the 16,500 Aeroplan points of course.

Confessions of a Points Addict

So what did I end up doing?

I scoured over Red Flag Deals (where other points addicts unite) and followed Saving Mentor’s suggestion for frequent transactions at Esso. Every $3 at Esso gives you 1 Aeroplan point.

Yes, you guessed it right. I ended up going to Esso, and did 3-5 transactions of $3 each time I went to get gas (I think I went about 6 to 10 times and did 3-5 transactions), I went to Home Hardware once for one transaction, and exchanged points on Points.com for a few points.

All these mini-transactions were legit and Aeroplan nor Esso had no issues with this, according to the rules and regulations of the points challenge.

The Low Point

I went to gas up at night usually, and actually felt adrenaline rushing through me as I made my $3 transaction. Then inserted the ol’ credit card for another $3 transaction. Then inserted my debit card for another $3 transaction. I felt like a points junkie. I would peer over the gas bar to see if the attendant was looking at me from the safety of his glass window. If I didn’t see any eye contact or suspicion, I would go ahead and try for another $3 transaction. I would peer again.

Early on in my Esso escapades, one of the gas station attendents came out, furious looking. He said to me “Stop it with the $3 transactions! Why three dollars? Why? Why is everyone doing this?”

My only reply was: “Other people are doing this?”

Suddenly, I didn’t feel so alone. The Red Flag Deal effect was on. Everyone else was doing the same thing.

The other low point was when the credit card became suspicious of the frequent, numerous transactions at Esso. They called me and I explained that everything was fine, it was just me who was doing the frequent transactions. I knew that this would happen (which is a good thing because that means that the security fraud protection team from the credit card company was actually doing their job) and this didn’t give me the same adrenaline rush as pumping gasoline at $3 each time did.

The Payoff…

After all that work (it was a lot of work), I was anxious to see whether it would pay off. Like many others on Red Flag Deals, I was waiting for the congratulatory email that said “Congratulations! You have earned 16,500 Aeroplan points!”

After a few weeks, that wonderful email came.

The payoff came when, after taking eons to earn Aeroplan points, I get a whopping 16,500 Aeroplan points credited to my Aeroplan account. Then I was able to use it for a short haul flight and a mini-getaway with my boyfriend. I saved over $200 (still had to pay about $70 of taxes and fuel surcharges and other yucky expenses for the free ticket).

In the end, I would do it again! It was a lot of work but also a lot of pay off. There you have it folks, I am a points junkie and I’m not afraid to admit it.

Readers, how far have you gone to score a deal? What are your confessions?