Massachusetts, United States

Dating in Gloucester

Meet real singles in Gloucester, whether you live here or are visiting.

Looking for singles in Gloucester? Gloucester is home to about 30,491 people, and The One Dating keeps your deck to real people near you, shows you who already likes you, and opens the chat the moment it is mutual. Here are a few first date ideas to try once you match.

First date ideas in Gloucester

  • Gloucester Fisherman's Memorial

    A walk here keeps a first date easy and free.

  • Annisquam Harbor Light

    A scenic stop with a story behind it.

  • Ravenswood Park

    Somewhere to talk while you take in the scenery.

  • Wingaersheek Beach

    Shoes off, phones away.

  • Sargent House Museum

    See what catches each other's eye.

  • Annisquam Exchange and Art Gallery

    Check the calendar and pick something new to you both.

Meeting someone new? Read our first date safety tips and how to spot a fake profile.

How The One Dating works in Gloucester

  • No bots and no fake accounts in your deck: every like is a real person.
  • Pick a Main Character Vibe so matches know your energy before the first message.
  • See who already likes you, and get a short list of Top Picks from the preferences you save.
  • Only matches can message you, and block or report takes two taps.

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Dating in Gloucester, MA: Meet Real Singles · The One Dating