By Dr. Jenn Mann
Updated Feb 14, 2018 @ 12:30 pm
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Hump Day 
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Welcome to Hump Day, where award-winning psychotherapist and TV host Dr. Jenn Mann answers your sexiest questions—unjudged and unfiltered.


I've been on a bunch of dates with a guy I really like, but we're not quite at that define-the-relationship stage yet. Is there a non-awkward way to celebrate Valentine's Day with him without coming on too strong? —New Bae


You are in the Valentine’s Day gray zone, and I don’t mean the Fifty Shades of Grey kind. Your relationship has a lot of potential but is new and undefined.

The way I see it, you only have four options:

1) Don’t say anything. Pretend V-Day doesn’t exist. Have a case of romantic amnesia. Hold out for him to ask you out for the big day. But if you take this route, you must be prepared for it not to happen. Understand that, this early in a relationship, not sharing Valentine’s Day doesn’t mean anything about your potential future together. Some guys don’t want to go all out until they are in a committed relationship and know it has legs.

2) Bring it up casually. Ask him if he is up for spending a low-key Valentine’s Day together. You can let him know that you enjoy his company and that you would love to have a fun night together. By doing this, you’ll also find out how he feels about the holiday—i.e. if he didn’t ask you to reserve Feb. 14, is it because he simply doesn’t like celebrating the pseudo-holiday or is it because he views it as a major deal, one that you’re not quite ready for. On that note, know going in that there are some guys who liken sharing Valentine’s Day to a walk down the aisle and think it's a sign of a huge commitment. If he is one of those, the idea of sharing this day of romance five dates in may leave him shaking in his shoes.

VIDEO: This Is How Your Favorite Stars Are Celebrating Valentine’s Day

3) Ask him out. Take the bull by the horns and ask him out for an evening you plan. Just keep in mind that this sets a precedent that, if you go the distance, you may be expected to do the asking and planning for romantic occasions. Some guys will love being asked out for Valentine’s Day, but others may feel slightly emasculated. Read your audience. You also have the choice of making this a capital-V Valentine’s Day date or simply organizing a date that happens to fall on Feb. 14 but isn’t characterized by red hearts and Godiva and staring into each other’s eyes over candle light. That’s okay too. Here are a few activities you can try if you’re not ready to propose the honeymoon suite:

  • Do something active: A hike or bike ride is romantic without feeling cliché. You’ll get to connect but in a way that’s a far cry from Hallmark’s portrayal of Valentine’s Day.
  • Netflix and grill: A regular night in with a romantic upgrade is a is a great way to celebrate V-Day in the gray zone. Cooking together while watching a movie is intimate but low pressure.
  • Your go-to: What have you done for your last several dates? Grabbed beers? Played pool? Gone for a walk? Do that. While you may not want to make a statement that you have to spend Valentine’s Day together, there’s also no reason you can’t have a date tonight just because it's Feb. 14. Textin “want to grab a drink tonight?” is always safe.
  • Opt for food or drinks as a low-key gift: Whether to buy your Valentine a present—and what kind—is a struggle even once you’re out of the gray zone. You don’t want to be the only one not to get a gift; you also don’t want to be the only one not to receive one. You don’t want to get something over-the-top; you also don’t want to go for a plush bear if your partner’s picking out jewelry. For couples (or something like them) in the gray zone, a small gag gift or something you pick up that’s thoughtful but casual and inexpensive strikes the perfect tone—and often that comes in the form of food or drinks. Save him a few cookies from a batch you made for your office and think he’d love or pick up a bottle of wine that you want to try together.

4) Make other plans. Doing this prevents you from losing your mind, hinting about the day, and feeling helpless as you wait for him to ask you out for The Big Day. Planning something fun with girlfriends is a great option. One year when I was single in my 20s, I organized a huge dinner with all my close single girlfriends and had a contest to see who’d had the worst date ever. It was a blast. The winner was treated to dinner and a bottle of wine. (Don’t worry, I didn’t drink the whole bottle all at once.)

Regardless of how things play out, you potentially have your whole future to share Valentine’s Days together so don’t make this a barometer of your future relationship together. Respect the gray zone, and make sure you do have something fun planned, whether with him or not, so you are not home alone feeling resentful or upset.

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