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Answering all those burning questions you didn’t know you had about home ownership.

The Shameless Ask

Picture of Jessica Dabkowski

Jessica Dabkowski

Helping you with all things homeownership!

Today’s article is inspired by several incidents in my personal life this week (Yes, so what else is new? 🤷🏻‍♀️) and the Super Bowl. Stick around if you want some tips to implement a technique I call the “shameless ask.”

As we approach the Super Bowl, you may be thinking about how you’re going to watch the big game. Maybe you’ll go to a party or a bar, but many of us will watch it at home. Will you be watching on your cable subscription? Maybe you’re a cord-cutter who is going to stream the game? Either way, let’s talk about the shameless ask.

The Shameless Ask

Once upon a time, I managed a multi-million dollar benefits program. There’s a (little) bit of pressure in managing a program that large. This role taught me many things, but the biggest lesson I took away from it was the art of the “shameless ask”. You want a six-digit refund on a program that failed to provide any substantive benefits? Ask and you shall receive. You want to hold the per member rate steady for another three-year term? You have to ask.

“So what, exactly, is the shameless ask?” you say. The shameless ask is what I call asking for something you want and not giving a crap if the response is a hard no. Often, it’s asking for more than what you want on the off-chance they give it to you. To be very clear, the shameless ask happens with all politeness, and in fact, is sometimes granted based on how you frame the request.

In Real Estate

I use the shameless ask – albeit, more cautiously – as a real estate agent all the time. Now, I always run the shameless ask by my clients along with the potential outcomes so they can determine what they are comfortable with in the ask. 

You want the grand piano thrown in? We can ask them to sell it to you for $1. The roof is failing and the A/C doesn’t work? We can ask for a juicy credit at closing to offset the investment required. We can ask for anything you want, we just have to navigate the people on the other side of the deal. (It’s a little different than dealing with a large corporation because there can be an emotional response in real estate.)

Mr. Owl, will the sellers throw in the piano?

In my personal life, I can be as bold as I want since I’m the person suffering any adverse consequences. The Mathematician is really just the beneficiary in this entire shameless persona of mine.

An Illustration

The Mathematician and I have an airline co-branded credit card that we got explicitly to enhance the comfort of our travel. For the record, I do not like to travel. The Mathematician absolutely loves it. This card is meant to help make me hate traveling slightly less by providing lounge access, priority boarding, random upgrades and free checked bags.  

This airline rolled out a bunch of changes last year, rolled some back, rolled out more this year and jacked up the annual fee another $100. I find out about these changes (via reddit, no surprise) with a post from a nice user who says he was offered 70,000 reward miles to keep his card open (i.e. not cancel). Well, hello, free miles!

The Mathematician gives me the side eye, but 20 minutes later we have 60,000 miles pending on our card for “being a loyal customer” and he’s high fiving me like I just received a Hail Mary pass.  What did I say to the rep? “I’m on the fence about canceling. What can you offer us to stay?” The credit card provider knows my value proposition and spits out a corresponding offer, which I happily accepted.

The Mathematician’s thoughts, exactly.

The point of my story is that I am not afraid to ask for what I want in a negotiation (or what my client wants!). A lot of the time you will get it. If I didn’t ask for those miles, we would never have received them.

Xfinity: A Case Study

Now, my weird aversion to travel aside, let’s discuss a shameless ask that may benefit you: negotiating your home cable and/or internet package. Now, I have Xfinity, née Comcast. I have some inertia at play here because I really don’t want to deal with moving my cable service. My Xfinity service has been (stunningly) reliable in the time we have lived in our current house. That being said, I’m not going to stomach a 33% price increase just because my “promotional rate” lapsed. 

The Due Diligence

There’s some due diligence you need to do before you contact your provider.  You need to research what competitors in your area are offering. I check in on Wow, AT&T and relative newcomer, Verizon, all available in my area.  Everyone was running $20-40 below my new monthly fee. Of note, WOW is currently offering a $5 monthly fee that allows you to keep your current internet rate into eternity. I was sorely tempted by this offer. (If you have WOW, you might want to jump on that deal.)

If you can figure out a way to see the new customer deals for your current provider, this information is incredibly powerful. It gives you an idea of their current rock bottom price for these plans. You might have to use a private tab in your browser, borrow a neighbor’s address or go use a public wifi so your current provider doesn’t realize it’s you looking at the new customer rates. 


Now that I’m armed with my leverage, I make the call to customer service. What a joke – despite me yelling “representative”, hitting the 0, 9, * and # button and dropping a curse word (tip: some systems will expedite you to a rep if they pick up that you are cursing), I can’t get through to a person. I am stuck in customer service menu loop hell. #goodjobXfinity

I give up and jump on the chat, where I’m actually quickly shuffled to a live rep who is quite happy to play the game with me.  Just keep typing “representative” until they push you through the bot to a live person.

The Dance of the Dragons

Let’s go over the basic flow of these conversations. After 15 years of doing this dance, the script doesn’t really change year over year.

Getting Started

Advise the rep that your promotional rate has lapsed or you are looking to cut costs.

The rep will either (a) tell you what a great deal you’re getting even without a promo rate, or (b) advise you he is happy to see what you are eligible for. It depends on the current script the reps have in front of them.

You should then share the new customer package information you gathered from competitors. “I shopped around and I see [insert competitor name] is offering [internet speed] for $[dollars]. Can you offer a similar rate? 

Change Tactics, If Necessary

If your company is offering an introductory deal, bring that up as well.  If they tell you that is for new customers only, ask “Okay, how long would I have to leave your service before I can come back at that rate? I’ve been curious about the services offered by [competitor] anyway.”

In my experience, this is where they tell you they can offer you a faster internet speed than you have for your current price or slightly less/more.  If you need faster internet, this might make sense for you. 

If you’re like us, you may have more speed than you even need. I always ask, well what if you drop me down a speed level? See what they come back with – this year, it was $10/mo more to drop my speed so that didn’t make sense. 

I think we all feel the sting of defeat this year.

For me, my sole goal this year was to keep our bill flat. Last year, I was thwarted and the sting of defeat basically ruined my February last year.  Our monthly bill went up $5/mo and that $5 was still rubbing me the wrong way.  


If you have cable and internet packaged together, ask about dropping the cable portion and keeping just internet. This nugget should really get them in a tizzy because the last thing they want is you to drop any service, but especially the dying cable service.

Here’s another topic you can use to push them on lower prices – “Is there a cancellation fee? How much is it? Is it prorated? I might just give [competitor] a try and see how their service works for me”. If you ask a lot of probing questions, sometimes they will just cut down to the rock bottom offer.  

If you suspect there’s more savings to be had, tell the rep you have to think about it and HANG UP THE PHONE. Call or chat back a different day to see if the promotions have changed.

The Final Volley

The most powerful thing you can do is cancel your service. I used this trick back in the day when we went on vacation. Angry and frustrated, I cancelled my service before we left. I just figured I’d deal with it when we got home. On the second day of our vacation Comcast was blowing up my phone with great deal offers to come back. I’m a geriatric millennial, though, so this was back in the day where we didn’t have “smart devices” that went crazy if the wifi went down.

Another time, I transferred my service to WOW, and I was getting the same calls from Comcast. Alternatively, if you have a roommate, switch the cable service over to the other roommate’s name if they qualify for the introductory offer.

In the end, I settle for 200 mbps faster speed for the same price I was paying previously.  Again, inertia, I don’t want to deal with installing a brand new line to the house and the rigamarole of setting up a new account with a competitor. Maybe you decide to make the switch.  Either way, I want you to feel empowered to take those 10-20 minutes to slash your monthly bill. I can think of lot of ways to spend the $240 I saved this year.

Tell me about your shameless ask. I want to hear about those things I might be missing or we wouldn’t think were negotiable!  

Thanks for joining me this week.  As always, I’m here to help you with all your burning homeownership questions.  

Photo by Aditya Singh

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