👯‍♀️ Get a year of BOGO flights

Happy Valentine’s Weekend, you lovebirds! 💝

This is your reminder that everyone deserves love this year. 

Your partner, your mom, your group chat, your neighbor’s cat… 

And yes, even the people standing two inches from the luggage carousel waiting for their bag. 

Even those people. 

In the spirit of romance and buy-one-get-one flights (my preferred love language), let’s recap the week.

🌟 Team Daily Drop is looking for a Full Stack Software Engineer and a Frontend Software Engineer — love building great products that help millions spend smarter and experience more? We’d love to hear from you.

💌 Delta is offering a 2x bonus on Delta SkyMiles for gift card purchases (ends Feb. 16). 

🏨 Marriott’s new global promo is live (and here’s how to get the most value). 

⛷️ How to watch the Winter Olympics for free (with credit card perks).

🎥 Don’t miss the ultimate guide to Hilton Honors in this week’s Daily Drop YouTube video.

🏆 Our Favorite Pick: Companion Pass is back, baby!

Every once in a while, Southwest drops the offer.

Yeah, you know what I’m talking about… and if you don’t… I’m about to rock your world.

Southwest’s co-branded cards just launched limited-time welcome offers: the ones that include a full year of Companion Pass PLUS a decent points stash after meeting the minimum spend.

If you’re newer here, the Companion Pass is basically Southwest’s best gift to humanity.

Here’s the deal:

• Book your own ticket with cash or points

• Add your companion (as long as there’s a seat available)

• They fly for just taxes and fees

• Use it as often as you want through February 28, 2027

That’s potentially a full year of BOGO flights (!!!).

But this time around is extra good, because… You earn tens of thousands of points as part of the welcome offer AND get an instant Companion Pass.

So really, you can book the first ticket with bonus points, and bring someone along for (almost) free.

Quick Example: Los Angeles to Hawaii

Let’s say you’re on the West Coast and want to hop over to Hawaii with your sister / best friend / situationship / emotional support human.

Southwest flies nonstop from LAX to Honolulu (HNL) for as few as 8,000 points each way (depending on the season).

That means you could book:

• Round-trip for about 20,000 points

• Add your companion

• Pay only their taxes and fees

Two people to Hawaii for the price of one award ticket. Eeeeekkkk, fun!

👉 Explore all of Southwest’s current card offers in Mike’s full newsletter breakdown.

✈️ Quick Hits: Two things worth knowing

This week, Mike (our points-and-miles Yoda) covered two fundamentals that every traveler should have in their toolbelt.

1. Do your points and miles expire?

Sometimes. Most programs just require activity every 12–24 months (a transfer, small redemption, dining portal purchase, etc.) to reset the clock. A few never expire, while a few are ruthless and expire no matter what. Know which bucket your points live in.

👉 Read: Do points expire?

2. What are positioning flights?

This is when you book a cheap flight to another city to unlock a better award deal from there. It’s not the most convenient option, but it can save tens of thousands of points. This is truly one of the best money (and points) savers out there.

👉 Read: Positioning flights, explained

Both of these are simple concepts, but mastering them makes you soooo much better at this game. So read up, friends!

🌍 Week in Review

• Monday: ⏰ Do points expire?

• Tuesday: ✈️ Positioning flights, explained

• Wednesday: 💘 The ultimate flight hack for couples

• Thursday: ⛷️ How to watch the Olympics for free

• Friday: 🍷 New points sweet spot to Italy

And that’s gonna wrap up this Valentine’s weekend, friends.

If they won’t commit to you… at least make sure they commit to being your Companion Pass partner. 😙

Love you, mean it. 

Byeeeeeeee,

40°39'41.4"N 73°56'22.0"W

With contributions by Mike Dodge