Dating Life Advice

I’m about to make the Boston Globe’s “Dinner with Cupid” my absolute bitch

Want to enjoy a meal on us and maybe meet the person of your dreams? Let the Globe Magazine play matchmaker. We’re looking for unmarried adult applicants for With Cupid, a column that matches two singles up for a blind date and then details evening out together. Of course we hope that sparks fly, but we’ll write about the even when things don’t go so hot.

To enter, you must be at least 21 years of age and a resident of Massachusetts, Rhode Island, New Hampshire, or Maine. You must be available for a date that we set up, agree to attend that date, and be willing to sign our declaration of eligibility and release. We will not provide transportation to or from the date, and we will reimburse dinners up to $100, but no more. If you go over, the difference is on you.


I’m in. Not even for the romantic aspect either (there’s no way a normal girl would sign up for this). I’m getting in the game strictly for economic reasons. I read through some of the past date write-ups, and they all suck. The common denominators include going out to dinner at an overpriced average restaurant, making awkward small talk throughout the meal, and awkwardly parting ways after. Fuck that.

What I am interested in is the $100 reimbursement. It seems like typically the blind date goes down at a nice restaurant. They usually get a drink or two, maybe an appetizer, and two entrees. That’s a pretty forgettable night that will add up to $100 fairly quickly. That won’t be the case when I inevitably get selected. Here’s my plan.

If you’re selected to be my blind date, prepare to eat before because guess what? We’re going to Coogans. How has no one thought of this yet? You know what $100 gets you at Coogans? 100 beers. Well actually 90, since we’ll be putting $10 towards the sleeve of nips I’ll inevitably sneak in, but you should have already known that. Keep up, sweetheart. (Also can I get that $100 as an advance before the date? Depending on my Venmo balance I’m not sure if I can front that type of dough)

The post date write-up alone would put the Boston Globe back in the black. It would single handedly save the newspaper business. I can picture it now. “Tim seemed nice enough until he hit beer number twenty six, when he began urinating in his own pants. I asked him if he needed to change his underwear, to which he responded ‘I’m not wearing any’. Oddly enough, that is when I began to fall in love with him. Unfortunately, that was the last I saw of him, until I found him three hours later in a 7/11 playing rock paper scissors with a homeless man over the last Big Bite™  Hot Dog. To be honest, I have never been so turned on in my life. I still can’t believe he went rock four times in a row.”

So I guess the next step is to fill out the online application:

(I messed up the screen shots so I’ll just copy and paste the questions in)

First Name Last Name: Timothy McCue

Enter Your Age: 22

Enter Your Phone Number: Redacted for numerous reasons (mostly because I don’t want Mitch Martinez’s mom having another medium to incoherently yell at me)


Enter Your Neighborhood: Various Orange Line MBTA Stations

What is your occupation?

Upon obtaining a degree in deal closing from ITT Tech, I started a non-profit I currently run called “Motivating Mongoloids”.  In addition to that, I also freelance as a seductive pool boy, and at night I’m a mixologist at Applebees.

Do you have pets? If so, what kind?

I don’t have a pet of my own, but I do strongly identify with dogs, as we both spent our younger years in cages and currently enjoy running around playgrounds. I’m also known to hump inanimate objects from time to time.

How would you describe your race/ethnicity? (If you’d prefer to be matched with someone of a specific background, let us know.)

Although on the outside I’m technically a Caucasian male, the most accurate description of my spirit and personality would be that of a middle aged, sassy black woman.

Describe your idea of a perfect Saturday, from morning until night.

I don’t have the time or energy to map out my ideal day, but basically picture every plot of every Matthew McConaughey movie fit into a 24 hour period. That’s my perfect Saturday.


So yea, I honestly can’t foresee a situation where I don’t get selected. After this blind date I’ll be the first person in Boston Globe history to be simultaneously featured in the “Dinner With Cupid” column and the “Obituary” section. Somehow I just continue to redefine journalism.





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