Dating by city / United States / Massachusetts / Chestnut Hill

Singles in Chestnut Hill, Massachusetts

Looking for a date, something serious or new friends in Chestnut Hill? Create a profile and you could be the first local on this page.

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Chestnut Hill at a glance

  • About 24,000 people live in Chestnut Hill.
  • It lies in Massachusetts.
  • It's about 185 miles to New York, the country's largest city.
  • For a bigger city, Newton is about 2 miles away.
  • Close by: Waltham (5 miles), Boston (6 miles) and Arlington (6 miles).

First-date ideas for Chestnut Hill

Chestnut Hill is small enough that you may have friends in common, so start with a relaxed coffee in the centre. If you would rather meet away from familiar faces, Newton is close by.

Staying safe

  • Meet in busy public places and tell a friend where you are going.
  • Never send money to people you met online.
  • Report and block anyone who makes you uncomfortable.

Questions about dating in Chestnut Hill

Who can I meet near Chestnut Hill?

More than 3.8 million people live within 30 miles of Chestnut Hill, in 146 towns and cities including Boston, Lowell and Brockton. You set the distance yourself in the filters, from 5 miles up to 300 miles — or choose “Any distance”.

Is there a free dating site in Chestnut Hill?

Yes, completely. Nothing on YADate is paid, in Chestnut Hill or anywhere else: you can browse, like, write first and send voice messages or gifts without a subscription or credits. Daily caps exist only to stop spam: up to 40 new conversations a day, for example.

Are the singles around Chestnut Hill real people?

YADate never creates fake profiles or writes on behalf of people who don't exist. A moderator checks every photo before it appears, every member confirms an email address, and any profile can be reported. If someone asks for money or rushes you onto another app, report them — a moderator will look into it.

Can I date someone from outside Chestnut Hill?

Yes. Pick any other city in the filters, at home or abroad, and YADate shows the people there.

Dating tips

Profile & photos

How to write a profile that gets replies

Your profile is your first hello. How to write a few honest lines and choose photos that make people want to start a conversation.

3 min read

First dates

First date ideas that are easy and safe

The best first dates are short, public and relaxed. Ideas that leave room to talk — plus simple safety habits that let you enjoy the meeting.

2 min read

All dating tips