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Meet Single Men Over 50 in Chicago
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International Dating
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Men
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American
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Illinois
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Chicago
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Over 50
36 - 70 of 100
Nino
Standard Member
54
•
Chicago, Illinois, United States
Seeking:
Female 40 - 90
Adventurous, passionate, and full of laughter,I be...
Adventurous, passionate, and full of laughter—I believe life is too short for boring conversations and missed opportunities! I’m someone who enjoys deep connections, spontaneous road trips, and finding joy in the little things. Whether it’s exploring a new city, getting lost in a good book, or having meaningful late-night talks, I love creating beautiful moments.
Jim
Standard Member
58
•
Chicago, Illinois, United States
Seeking:
Female 48 - 60
Robin
Standard Member
52
•
Chicago, Illinois, United States
Seeking:
Female 40 - 99
Love will always win
Humble and honest man
Claudia
Standard Member
Verified
56
•
Chicago, Illinois, United States
Seeking:
Male 45 - 60
Jason
Standard Member
57
•
Chicago, Illinois, United States
Seeking:
Female 41 - 60
Kind soul seeking something real
I’m an easygoing and thoughtful person who loves good conversation, laughter, and trying new things. I enjoy [your hobbies — e.g., exploring new places, cooking, watching football, or relaxing with a good book]. I value honesty, kindness, and a sense of humor. I’m here hoping to meet someone genuine, build a strong connection, and see where it leads.
Bruce
Standard Member
53
•
Chicago, Illinois, United States
Seeking:
Female 30 - 47
Kind loving n. Caring. Gentlemen
I. Am. Kind. Affectionate loving caring. I like. To. Spoil. My. Partner
Tunis Chris
Standard Member
57
•
Chicago, Illinois, United States
Seeking:
Female 40 - 60
Dolph
Standard Member
52
•
Chicago, Illinois, United States
Seeking:
Female 48 - 80
no great discovery was ever made without a bold gu
choose the one who makes your life beautiful and colorful.
David
Standard Member
59
•
Chicago, Illinois, United States
Seeking:
Female 25 - 45
Brendan
Standard Member
52
•
Chicago, Illinois, United States
Seeking:
Female 34 - 54
Chris
Standard Member
58
•
Chicago, Illinois, United States
Seeking:
Female 47 - 80
I'm a calm loving person.
I'm a good lovely person, with passion for humanitarian services.
franklin
Standard Member
51
•
Chicago, Illinois, United States
Seeking:
Female 30 - 60
Good vibes 😎
Big on fitness, healthy living, and good vibes. I’m a softie who loves to cook and watch movies on quiet nights. Believe in real love, trust, and building something that lasts
Tony
Standard Member
53
•
Chicago, Illinois, United States
Seeking:
Female 28 - 46
Happy and blessed
A single man who is about to retired and travel the world. Looking for my new best friend here to possibly be a potential new wife.
Frank
Standard Member
56
•
Chicago, Illinois, United States
Seeking:
Female 51 - 83
Mell
Standard Member
55
•
Chicago, Illinois, United States
Seeking:
Female 35 - 46
Robin
Standard Member
55
•
Chicago, Illinois, United States
Seeking:
Female 20 - 41
Puerto rican currently living in chicago, I enjoy...
Sanjay
Standard Member
58
•
Chicago, Illinois, United States
Seeking:
Female 18 - 65
Mario
Standard Member
56
•
Chicago, Illinois, United States
Seeking:
Female 45 - 65
Looking for my woman lover and best friend
I don't drink smoke or do any type of drugs I workout at the gym I listen to smooth music and I am an honest and trustworthy man and expect the same
Dwight
Standard Member
52
•
Chicago, Illinois, United States
Seeking:
Female 55 - 75
Let it be love
i am open minded intelligent man and seek the same in a mate i would prefer a woman that is open minded open to new and thrilling changes someone that makes changes not imposes them on others like me.
Frederick
Standard Member
52
•
Chicago, Illinois, United States
Seeking:
Female 18 - 52
Looking for locals
Tall, athletic professional
Dali
Gold Member
51
•
Chicago, Illinois, United States
Seeking:
Female 29 - 48
Looking for a life-long relationship
I love to travel, have fun, hike, restaurants, and quiet nights at home watching movies. I am very loyal and trustworthy when in a relationship. I believe in love and am looking for a woman to spend the rest of my life with.
Mustafa
Standard Member
54
•
Chicago, Illinois, United States
Seeking:
Female 32 - 50
A kind and respectful type of person.....
Looking for a life partner
Edgar
Standard Member
59
•
Chicago, Illinois, United States
Seeking:
Female 30 - 49
Edgar
Single man looking for a simple minded other half.
Nardo
Standard Member
53
•
Chicago, Illinois, United States
Seeking:
Female 23 - 36
Chicago Friendly
Just looking, I never been married, I have no kids, I'm in my mid 40's...I enjoy the big city nightlife and simple life.
Bryant
Standard Member
57
•
Chicago, Illinois, United States
Seeking:
Female 32 - 52
LOOKING FORWARD TO GETTING TO KNOW U BETTER
FUN LOVING, DOWN TO EARTH GUY, WHO LOOKING FOR A HONEST, CARING PERSON
George
Standard Member
Verified
56
•
Chicago, Illinois, United States
Seeking:
Female 34 - 65
Enthusiastic
Single
Dion
Standard Member
53
•
Chicago, Illinois, United States
Seeking:
Female 30 - 50
Looking for that special woman.
I'm originally from Belize but Live and grew up in the Chicagoland area. I love to travel, listen to different types of music and try new foods.
john
Standard Member
55
•
Chicago, Illinois, United States
Seeking:
Female 18 - 38
looking for you
add later
Kent
Standard Member
Verified
53
•
Chicago, Illinois, United States
Seeking:
Female 30 - 50
Kent
separated
Joe
Standard Member
55
•
Chicago, Illinois, United States
Seeking:
Male 50 - 75
Karatejoe
I’m a poet, professor, flight attendant (37 yrs), black belt in karate, PADI scuba diver, soon to be licensed skydiver, theater and museum enthusiast, lover of long walks.
Phillip
Standard Member
58
•
Chicago, Illinois, United States
Seeking:
Female 34 - 53
Widower Seeking Companionship
Widower looking for compatible female.
Tony
Standard Member
58
•
Chicago, Illinois, United States
Seeking:
Female 34 - 53
looking for honest and loyal
self starter
Eric
Standard Member
55
•
Chicago, Illinois, United States
Seeking:
Female 32 - 50
Looking for the right one.
I'm down to earth. Family oriented. Goal minded, and fun.
DAVID
Standard Member
52
•
Chicago, Illinois, United States
Seeking:
Female 30 - 54
Looking for my last dance partner
Single, hard working and self employed, with travel to the world in my life
Tom
Standard Member
Verified
58
•
Chicago, Illinois, United States
Seeking:
Female 29 - 49
Be adult pewith,completed profile, at lest 2 pics.
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