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Matchmaker Chicago for singles over 40 and 50, in every season

MatureMeet VIP Concierge is a matchmaker for Chicago singles over 40 and 50, sold as a monthly subscription instead of a package. For $149 a month, or $74 a month billed yearly, you get an intake call, a rewritten profile, up to 4 hand picked introductions to verified members a month and first dates planned for the season you are in.

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A woman and a man in their mid forties laughing on an autumn walk through a city park with coffee
Verified Looking for long-term
A woman in her mid fifties on a video call with her matchmaker, taking notes at home

What does a matchmaker in Chicago actually do for you?

A good matchmaker saves you time and protects your energy. Instead of reading hundreds of profiles, you read a handful that someone has already checked for intention, values and distance. Instead of planning, you show up. At MatureMeet the concierge also watches for something many Chicago matchmakers never mention: romance scammers, who often target people over 50.

Is Chicago a good city for dating over 50?

It is a city of neighbourhoods, and that helps. People tend to stay close to home, know their local spots and plan around the L or the Metra. The challenge is the calendar. Winter shrinks social life for months, and summer fills every weekend at once. A matchmaker who plans with the seasons in mind makes the difference.

Who uses a matchmaking service in Chicago?

Mostly busy people. Doctors and lawyers in the Loop who work long hours, recently divorced parents in the suburbs whose children have left home, and widows and widowers in neighbourhoods they have lived in for thirty years who do not know where to start again.

Chicago neighbourhoods and suburbs your concierge plans around

You tell your concierge whether you will cross the city for the right person or would rather stay on your train line. Introductions follow that choice.

  • North Side: Lincoln Park, Lakeview, Andersonville, Edgewater and Rogers Park.
  • West and near west: Wicker Park, Bucktown, Logan Square and the West Loop.
  • South Side: Hyde Park, Bronzeville and Beverly.
  • North Shore: Evanston, Wilmette, Winnetka and Highland Park.
  • West suburbs: Oak Park, Hinsdale, Naperville and Wheaton.

First date ideas in Chicago by season

Winter Date ideas your concierge suggests a museum afternoon, a jazz or blues set, a cooking class, a warm neighbourhood café Why it works after 50 indoors, easy to reach, built in conversation
Spring Date ideas your concierge suggests a conservatory visit, a walk along the lake as the weather turns, a small theatre matinee Why it works after 50 light, daytime, low pressure
Summer Date ideas your concierge suggests the lakefront path, an outdoor concert in a park, an architecture boat tour on the river Why it works after 50 the city at its best, plenty to talk about
Autumn Date ideas your concierge suggests a walk through a forest preserve, a farmers market, a wine bar with a fireplace Why it works after 50 cosy without being too formal

Your concierge suggests a venue near both of you, sets the time and sends reminders. If the weather turns, a plan B is already in your message.

Events for singles over 40 and 50 in Chicago

Inside your account you see local events for 40 plus and 50 plus singles, RSVP and see who else is going. VIP members get priority places.

  • Blues and jazz evenings with reserved tables.
  • Theatre nights with a drink before the show.
  • Cooking and wine classes in small groups.
  • Architecture walks downtown.
  • Volunteer days, which are one of the easiest ways to meet someone kind.

See singles events for over 50

How VIP Concierge works for Chicago members

  • You book your intake call by video or phone from your account. It is part of the service, not a sales call.
  • Your concierge reviews your photos, gives photo guidance and rewrites your profile.
  • You receive up to 4 hand picked introductions a month, each with written reasoning.
  • Every person you are introduced to is verified with a selfie check matched to their photos and phone verification.
  • Your concierge plans the date and sends reminders, and any report you make is reviewed within 2 hours.
  • You keep full Premium access, so you can also search, message and send voice notes yourself.

Chicago matchmaker cost compared

Local matchmaking firms usually sell packages for several months at a time, commonly priced in the thousands of dollars and paid in advance.

Price Typical Chicago matchmaking firm thousands of dollars per package MatureMeet VIP Concierge $149 a month or $888 a year
Contract Typical Chicago matchmaking firm fixed number of months MatureMeet VIP Concierge monthly or yearly subscription, cancel in Billing
Introductions Typical Chicago matchmaking firm set by package MatureMeet VIP Concierge up to 4 a month with written reasoning
Member verification Typical Chicago matchmaking firm varies MatureMeet VIP Concierge every member verified before messaging
Scam shield Typical Chicago matchmaking firm not usually MatureMeet VIP Concierge built into every conversation

Not ready for a concierge? Premium is $39 a month or $19 a month billed yearly and gives you the verified community, compatibility test, video and voice.

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Questions and answers

Can I meet people from the suburbs and the city?

Yes. You decide the radius, by miles or by train line, and your concierge introduces people inside it.

What if I only want to date in summer?

You can cancel at any time in Billing and keep access to the end of the paid period. Winter can be a good time to meet, because life is quieter.

Is the intake call a sales call?

No. You have already paid for VIP Concierge when you book it. The call is your concierge getting to know you.

A couple in their mid fifties sharing an umbrella on a rainy London terraced street

Start with your Chicago matches

Enter your ZIP code and see a preview of matches near you. Creating an account comes later.

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