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The “day of” D* and Rishi’s Anthony Hamilton Proposal

Pulling off THE proposal at the end of an Anthony Hamilton concert was the culmination of a full development project plan. That being said … I did wage a twitter, email, phone and blog campaign to pull this off … here is the letter I wrote him from my blog. In fact, I have to say that it was the most detailed project plan I’ve managed since all the resources I required didn’t actually exist on our own. I won’t bore anyone with all the details prior to the “day of” the proposal … it’s too long and boring! Anthony Hamilton Proposal

Q: Why bother writing this entire spiel … isn’t it a bit over the top and arrogant?
A: Have we met? If you’re going to ask this question … I would normally try to piss in your coffee and call it Kahlua but I’m writing this for four reasons

  1. Lack of applicable resources: I actually found that planning anything like this, requires a ton of work and there is NO right or wrong way to do it. I did find that there were very few resources I could count on for any sort of guidance in the planning process.
  2. Women love details: I’ve also been told that women love the details and although everything worked out wonderfully, the new fiancée needs to know how much actual thought and planning went into this – I need to draw on this post in the future when I inevitably screw up
  3. Sharing our story: How else could I tell a complete story every time … at some point in the future I’m going to forget the details of the process – we all do. This helps us document a moment in both our lives.
  4. It’s a great travel story: Even for a traveler like me, sometimes the best place to do something is close to home. I tend to forget that sometimes.

Like watching Agent Jack Bauer on 24, there were multiple things to manage. Multiple storylines with multiple actors and random events, so here are the list of missions I had to accomplish on the day of the proposal.

Mission #1: The flight/taxi nightmare!
With D* and Eryn being in Detroit, I now had to get to Detroit to make the final execution (“Go-Live” in project management terms) possible. So I leave home at 7:15am to catch my 8:55am flight to Detroit. In typical fashion, I got there at 7:51am with the 7:55am cutoff time looming ( Canada-US check-in deadline is 60 minutes). No stress … the Air Canada Super Elite line typically has than one person or less waiting for assistance … Don’t attempt to check in like this without some type of status.

  • Turbulence sign #1 – 8:10am: Flight was delayed from 8:55am to 10:55am … ok no problem. I’ll get into Detroit at 12:20pm. We’re still good! I continue with breakfast and watching cricket online.
  • Turbulence sign #2 – 9:10am: Flight was delayed from 10:55am to 12:55am … ok this isn’t really happening … I’ll get into Detroit at 2:20pm. It’s going be tight, but I’ll make it
  • Turbulence sign #3 – 10:10am: Flight got cancelled. Ok, now I’m pissed. I called the Air Canada concierge in Pearson International Airport … Cheryl went through a couple options with me on the phone and we settled on a flight to Windsor, Ontario and then me taking a taxi from Windsor to Detroit. Of course Air Canada would pay the taxi fare.

Kudos #1: Cheryl (A/C Concierge) really came through for me here. She was calm, got back to me very quickly when she had to do her research and personally came for me in the lounge to escort me through the gates, back through Canada customs and into the other terminal by passing all the security. She was definitely excited when she saw the ring and I told her the reason I had to be in Detroit. Air Canada Management – here is another huge plus for having that type of service for your best customers.

So finally after everything, I got into Windsor around 2pm. The taxi ride from Windsor to Detroit is actually a very standard trip. The border is quite fluid and trivial, and there are thousands of people crossing daily in both directions for work – so this shouldn’t be a problem right?
Since I was proposing, it obviously had to go wrong … it seems that I got a border guard who had PMS or just didn’t like the fact that I had a TN-1 visa in my passport or didn’t like the fact that a Lebanese taxi driver was transporting a brown guy across the border. So the car got searched for an hour – while we just sat in the customs office. Yet another waste of time … in the end, I got into Detroit around 3pm.

Mission #2: Getting the tickets in hand … not so easy eh?
While I got to Detroit on time, another logistic difficulty was figuring out how to get the tickets from the Fox Theater to the hotel without D* suspecting anything. If she knew I was in the hotel, the surprise would be blown. If she knew that only I could pick up the tickets, the surprise would be blown. You get the idea.
After the taxi nightmare, I got to the theater and the tickets weren’t ready as they were VIP tickets. They would only be ready at 6:30pm. Well my reaction at the box office went something like this …

<R> What do you mean six [email protected][email protected] thirty … I just flew in from !$$!#%@ Toronto through Windsor for these tickets here. I can buy a $30 ticket and get that immediately, but I have to wait till 6:30 to get tickets that are worth a couple hundred bucks a piece? WTF? Call someone and fix this!!!
<Poor Sad Ticket Person = PTSP> I’m so sorry Mr. Sankar, but we actually don’t control VIP. I will call the manager.
<R> Ok … get it done
<PSTP> 8 minutes later> I’m sorry Mr. Sankar, but we rely on Mr. Hamilton’s crew for the VIP

So what to do now?

When in doubt, why not call someone on Anthony Hamilton’s crew? Thankfully, in trying to organize the stage walk on – Reece Hamilton and I were in constant contact. So I called him and explained the problem and he solved the problem immediately. D* and Eryn would check-in directly with him at the VIP desk and he would give them their tickets.

Boom!!! Problem solved and disaster averted.

Mission #3: Create distraction for D* to throw her off any possible suspicion.

D* called me while I was checked into the hotel. While on the phone, the hotel delivered her favorite flowers: Gereba Daisies along with an oversized cupcake with a random “Happy Birthday” icing message on the plate and random card. This idea was designed to throw her off any possible suspicion of me being in Detroit.

Kudos #2: The staff at the Westin Book Cadillac was absolutely phenomenal in helping me organize all the logistics at the hotel. When I first started coming up with the plan in July, Andrea Sobanski (concierge) and Susan Laing (Service Express Manager) were instrumental in offering great suggestions, ideas and helping coordinate things remotely. Andrea was a great resource in keeping me calm and steady when all ticket fiasco was going on.

The flowers and birthday cupcake were delivered on time and created enough of a distraction that when D* messaged me on Facebook to tell me how much she loved the cupcake and flowers, I knew that she really wasn’t clued in.
Important note to men : When you’re not romantic at all, any little thing you will be greeted with happiness, even a cupcake and flowers.

In the end

Distraction successful and suspicion averted

Mission #4: Collect my ticket, get backstage, coordinate with Reese Hamilton (Anthony’s brother) and avoid D* until the big reveal.

You would figure that coming into the theater, getting tickets and getting backstage to wait till the end of the concert should have been quite simple, however there were a couple complications such as :

  1. I had no idea what Reece looked like
  2. I didn’t know where the VIP room would be in relation to the Theater entrance
  3. D* has a small bladder – hence she could have been roaming around looking for a toilet and accidentally run into me
  4. I didn’t have a ticket and the box office had a huge line up – increasing the possibility of an accidental run in
  5. I actually didn’t have the words I would say on stage … in my head or on a piece of paper. (Which is why I “fumbled” on stage)
  6. I was nervous as [email protected]$! … I might have forgotten to say that – plus the staff was giving me lots of free drinks.

While I was completely figuring out things on the outside and not really having a plan, D* and Eryn were inside enjoying all the spoils of the VIP reception. It did help, that I sent along a couple pictures of D* and my blog post to read from our previous meeting with Anthony in New York – so he mentioned her turquoise scarf from the first meeting – the man is smooth I tell you.

Having drinks and appetizers with the posse. The girls had a great time in the VIP pre party since it was such a small gathering of people.

During the girls’ VIP shenanigans, I eventually got in contact with Reece (he found me wandering outside the theater) him and one of the backup singers, discussed plans and met with the security and backstage staff – got my ticket, VIP pass and backstage pass. After that the only question would be where I would hang out during the concert and when I would walk out onstage. To quell my nerves, I had one or four adult beverages and made friends with the bar staff. I must say that the staff were all super excited when they heard my plan and my execution. They were even more impressed with the ring … (blatant plug … choosing a Tacori ring and diamond was the best decision – D* made)

So while I was making friends, getting tipsy and sweating the details, D* and Eryn continued having their best concert experience ever.


As you can tell, D* was enjoying her center front row tickets … those were worth every penny, especially since it meant that I could spy on her from the balcony and from backstage.

Until that point, it was “THE.BEST.CONCERT.EVER” … from the girls’ perspective.

Mission #5: Get on stage, not choke or create a YouTube moment and get the words out.
Here is how I did!


After all the prep, everything went smoothly and I didn’t throw up because of my nerves. So after the concert, we headed out with Anthony’s crew for an after party, late night dinner and one or two more adult beverages.
By the way … Eryn has a crazy thumb trick … that astounded Anthony … look at the bend in her thumb!

And that folks is the story of the “day of” …. with a twitter RT by Anthony 😀


Anthony Hamilton Proposal

About Rishiray

Rishi Sankar is a Cloud HRMS Project Manager/ Solution Architect. Over the past 15+ years, he has managed to combine his overwhelming wanderlust with a desire to stay employed, resulting in continuing stints with 3 major consulting firms (IBM, Deloitte, Accenture). He documents his adventures around the world on “Ah Trini Travelogue” with pictures and stories from the road/tuk-tuk/camel/rickshaw. You can follow him on Twitter at @rishiray and on Facebook at “Ah Trini Travelogue . He doesn’t like Chicken Curry but loves Curry Chicken and is always trying to find the perfect Trinidadian roti on the road. He also doesn’t like cheese and kittens … and definitely not together. E-mail from his blog is appreciated like a 35 yr old Balvenie at [email protected]

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  • Skyhawk73

    Congrats and thank you for sharing your special moment with your friends. Wish you much happiness ahead…

  • Cindy Konkin

    Awwww… that was so wonderful!!! Diane deserves the very best and that was one romantic proposal to start it all off with! Congratulations to both of you!!

  • The trip is so good, it’s interesting to read.