Valentine’s Day has a way of pressuring couples into impersonal, default choices: an overpriced (and crowded) dinner, a last-minute card from Walgreens, a box of chocolates grabbed on the way home. There’s nothing inherently wrong with any of that, but if you want the day to actually mean something, it helps to be a little more intentional.
Over the years, we’ve published a wide range of posts on dating, gift-giving, and building strong relationships. Below, we’ve rounded up some of our best Valentine’s-related and adjacent guides, from creative date ideas and thoughtful gifts to deeper relationship check-ins. With a little bit of forethought, you can break through the shallow, commercial nature of the holiday and plan a day (or even just a conversation) that feels personal, memorable, and genuinely worthwhile.
Date Ideas
Going out to a nice restaurant is standard protocol for a Valentine’s Day date, but it isn’t very original and dining out on such a busy night isn’t always that enjoyable, anyway. Why not mix it up by planning an out-of-the-box date — a novel activity out on the town or in the intimate atmosphere of your own home? Whatever you end up doing, make sure you dress nicer than usual to make the occasion feel special!
- Cheap Date Ideas She’ll Actually Love
- 15 Creative Date Ideas
- At-Home Date Night Ideas
- How to Create the Ultimate At-Home Fondue Date
- Take Her Around the World for Valentine’s Day . . . Without Leaving the Kitchen
- The Perfect Valentine’s Day Menu
- A Man’s Guide to Smart Casual Dress
Gifts & Gestures
While a woman will often say she doesn’t want anything for Valentine’s Day, what she often means is that she doesn’t need anything expensive and elaborate. But, she’s probably still hoping for a love note and/or flowers at the least. You can’t go wrong with giving her both, and we’ve got some tips for making these gestures more meaningful below. If you want to also give a gift, that will likely be appreciated, too. Extra points if it’s homemade.
- How to Write a Love Letter
- How to Give Flowers Like a Victorian Gentleman
- 7 Romantic, Non-Lame DIY Valentine’s Day Gift Ideas
- How to Give a Gift to a Woman
- Huckberry’s “Gifts for Her” shop
Relationship Check-In
The approach of Valentine’s Day is a good time to assess the status of your relationship. Are there things you can do to improve it? Should you even still be dating this person?
- How Do You Know When She’s the One?
- Podcast: How to Keep a Happy Relationship Happy
- The Yearly Marriage Checkup
- 10 Ways to Be a Better Husband Today
- Look Before You Leap: Questions to Ask to Avoid Falling in Love With the Wrong Person
- Podcast: How to Avoid Falling in Love With the Wrong Person
- 14 Red Flags to Look Out for in a Relationship
