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Cigar & Whisky Pairings For Every Stage Of Your Relationship (The Men’s Valentine’s Day Gift Guide)

Cigar & Whisky Pairings For Every Stage Of Your Relationship (The Men’s Valentine’s Day Gift Guide)

Typically, Valentine’s Day is marketed as an unofficial holiday for the ladies but at YouGottaEatThis we understand that men need love too, so myself along with the homie Anthony “AB” Benson decided to cater to the bruhs this year. Similar to our female audience, depending on how long you’ve been in your relationship the level of gift giving can be kind of tricky.

The good news is men are simple creatures and to make Valentine’s Day memorable for your special guy only requires two key components: quality cigars and good whisky!

Below I have chosen the drinks, while “AB” provided a handful of cigar pairings for every stage of your relationship to assist you with speaking the language of love to your man. Cheers!

Dating 1 – 6 months: George Dickel No. 12 Tennessee Whisky & Crown Royal Northern Harvest Rye – Price range: $25 – $30

  • George Dickel Tennessee Whisky is known for their signature chill charcoal mellowing which makes it the smoothest sipping whisky around.
  • Recently crowned the 2016 World Whisky of the Year by Jim Murray’s Whisky Bible, Crown Royal Northern Harvest Rye is meant for the loved ones you think are world-class.

Cigar Pairing: Romeo y Julieta – $6.30 – $105.00 – Medium

A starter cigar, Romeo y Julieta has a nice medium body smoke that goes well with George Dickel No. 12.  Romeo y Julieta is a classic brand that offers exceptional construction and a smooth and creamy taste and aroma. If you enjoy a pleasant-tasting cigar that is not overwhelming yet is very satisfying, then Romeo y Julieta cigars are for you. They’re the perfect way to say I like you without being too forward!

Shapes: BelicosoChurchillCigarillosCoronaLancero/PanatelaRobustoToro
Wrapper: Indonesian
Origin: Dominican Republic


Dating 6 months – 1 year Spirit: I.W. Harper Kentucky Straight Bourbon Whiskey & Bulleit Bourbon – Price range: – $30 –$35

  • After 20 years abroad, I.W.  Harper Kentucky Straight Bourbon has come home to the U.S. to satisfy significant others struck with wanderlust.
  • Bulleit is a staple, whether included in a Hot Toddy, Old Fashioned, or enjoyed neat or on the rocks. It’s a must-have in any liquor cabinet.

Cigar Pairing: My Father – Cedros Deluxe Cervantes $13.00 – $190.00 – Full Body

After 6 months you’ll want to give your dude a cigar that shows you really care. One of the best ways to do so is with a “My Father” Cedros Deluxe cigar. The Cedros Deluxe Cervantes is a beauty to behold. The medium brown wrapper bears the striking, intricate My Father crest and a full body profile. The hand-selected long fillers are grown on the famous Garcia family’s farm in Esteli, Nicaragua, and the 44 gauge ring and 6.5 inch body make the Cedros Deluxe Cervante a long, luxury cigar with expertise packed into every puff making it ideal for those past the dating stage in your relationship.

Shapes:  Parejo
Wrapper: Habano Rosado
Origin: Nicaragua

Long term relationship: Orphan Barrel’s Rhetoric 21-Year-Old Kentucky Straight Bourbon Whiskey

  • Progressively aged with hints of baked caramel and cinnamon, Rhetoric 21 is part of the Orphan Barrel Project where nearly forgotten whiskeys are resurrected from the depths of distilleries. There’s no doubt he will geek out over this fact.

Cigar PairingPadron 1964 Anniversary Series – $17.00 – $255.00 – Full

You’ve put consistent work in. your relationship is solid, and now you two love birds are cruising into settle down territory. Making such a bold statement and ever-lasting impression, requires a special kind of fire. Otherwise known as the Padron 1964 Anniversary Series.

These gems are handmade to celebrate 30 years of producing some of the most exceptional and sought after premium cigars in the world, and are to die for! This top-of-the-line, flawlessly constructed gems are on the fuller size in strength and body and feature the most enjoyable flavors of espresso, earth, chocolate, and nuts with a great toasty finish. They are box-pressed, packed in cedar boxes of 25. Get ’em after your three to five year mark!

Shapes:  Parejo / Box Press
Wrapper: Nicaragua
Origin: Nicaragua

“The Married & Comfortable Stage” Spirit: Blade & Bow 22-Year-Old Kentucky Straight Bourbon Whiskey  and Crown Royal XR LaSalle – Price range: $130 –$150

  • Blade and Bow 22-Year-Old Kentucky Straight Bourbon Whiskey is a limited release whiskey that pays homage to the artful passion and renowned craftsmanship of the legendary Stitzel-Weller Distillery and winner of the coveted double gold medal from the San Francisco World Spirits Competition.
  • The second addition to the Crown Royal Extra Rare Whisky Series is an exquisite blend crafted to include a small reserve of the final batch of whiskies that were saved from the renowned LaSalle Distillery. A special blend to elevate any romantic evening!

Cigar Pairing: Ashton VSG Eclipse Tube · 6 × 52 – $25.00 – $308.00 – Full

If you want to get your husband a surprise gift like say, for his born day, then the VSG Eclipse has it all: a dark brown sun grown wrapper packed in a sleek and elegant jet black tube, complimented by smooth Dominican filler. This spicy number makes you feel special all year round!

Shapes:  Parejo / Box Press
Wrapper: Ecuador Connecticut
Origin: Dominican Republic


Hopefully this gift guide comes in handy and will help you select the perfect smokes and drinks for your boo’s collection. All men love a great cigar & a neatly poured drink and nothing warms their hearts like a good puff, smooth pour and stimulating parle!

Happy Valentine’s Day!

About The Author

Ru Porter

Foodie. Music Nerd. Sneakerhead.

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