Valentine's Day is this weekend (Sunday, February 14th, boys) and if you haven't made reservations yet you'll definitely be scrambling for a place to dine Sunday evening in the Portland area. There's tons of places to pick but what restaurant is perfect for your relationship? Are you newly married or going on a first date? Those occasions call for two very different meals and settings. This guide will make the choice a little easier.

  • 1

    First Date via Lauren T. via Lauren T.

    The North Point
    35 Silver Street

    The North Point has some of the most delicious martinis in town and the atmosphere is a cozy, laidback brand of romantic. Nothing on the menu is too intimidating for a first date. The flatbreads are delicious and they’re not too messy (because who wants to be cleaning food from your face on a first date?) I recommend enjoying a D’Anjou Pear Martini or a Cucumber Gin Martini with a Havana Cubano stuffed flatbread sandwich. You’ll get comfy on the pillow-covered benches with the ambient light.

  • 2

    Dating 6 Months via Linda Y. via Linda Y.

    41 Middle Street

    Yelp Reviewer Ana Laura M. says, “Probably a candidate for the best meal of my life.” Many reviewers point out that this location is a great spot for dates. The combination of exposed brick and authentic Italian cuisine is sure to impress your partner at any time in your relationship, but it’s not too fancy to make ‘em think you’re rushing the romance. Try any of the handmade pastas.

  • 3

    Dating One Year via Stephanie W. via Stephanie W.

    The Grill Room
    84 Exchange Street

    If you’ve been dating for about a year, this could be near your first Valentine’s Day together. That, combined with the fact that you’ve spent 365 days with the same person, is reason enough to try out one of “The Rooms”. The Grill Room is a steakhouse with a upscale casual ambiance.

  • 4

    Newly Engaged via David John A. via David John A.

    Five Fifty-Five
    555 Congress Street

    This classy establishment has been recognized by Trip Advisor, Open Table, Wine Spectator, and Food & Wine Magazine and it’s no surprise when you see the Master Chef-esque plates. Reviewers have said, “The lobster mac and cheese is something every person needs to try it has an amazing balance of flavors and is heaven on a fork,” and, “The place had a lovely ambiance with very interesting second floor seating. Looked like a fun place to be – up on high looking over the other diners.”

  • 5

    Newlyweds via Tony S. via Tony S.

    15 Chestnut Street

    Yelp Reviewers said, “The atmosphere was like nothing like what we have ever experienced. The restaurant is in a converted church.” The interior of Grace is one of the most stunning settings in Portland and possibly Maine. If this year is your first Valentine’s Day as a married couple, you’ll love Grace for the architecture and stained glass as well as the food.

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    Married 5+ Years via Alexis T. via Alexis T.

    Takeout from OTTO Pizza
    576 Congress Street + More

    Listen, you could do this at any phase of your relationship and guaranteed your girl will think it’s adorable and cozy and perfect. Forget the stress of picking the right outfit or wondering which fork to use for your petite pre-dinner salad. Dive into a Mashed Potato Bacon Scallion and binge watch Netflix.

    Actually, I've decided to do the new list and it's just going to involved all the places for takeout dates.

  • 7

    Single and Loving It


    YOU. DO. YOU. My kings and queens, own your singleness. Order delivery from and have a dance party in front of your full length mirror. Or grab your other single pals and go to a dive bar with karaoke. Or sit around in a Chicago Bulls onesie eating cheeseburgers with your BFF. Seriously, LOVE YOURSELF FIRST and eat wherever the hell you want.

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