Login

Meet Single Men Over 50 in Chicago

View Singles Now
Review your matches for free
Access to advanced messaging features
Trusted site backed by Cupid Media
International Dating

/

Men

/

American

/

Illinois

/

Chicago

/

Over 50

36 - 70 of 100
Tim
55 • Chicago, Illinois, United States
Seeking: Female 32 - 51
Gifted
Man of integrity, honest, loyal, and friendly.
Joe
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
58 • Chicago, Illinois, United States
Seeking: Female 34 - 53
Widower Seeking Companionship
Widower looking for compatible female.
Tony
58 • Chicago, Illinois, United States
Seeking: Female 34 - 53
looking for honest and loyal
self starter
Mark
57 • Chicago, Illinois, United States
Seeking: Female 18 - 60
‘Seeking Asian bf to relocate to the US for LTR
I enjoy motorcycle riding, have 2 dogs, like working out and working on my truck.
Kevin
55 • Chicago, Illinois, United States
Seeking: Female 18 - 45
Great guy whiting.
I am very outgoing and very fun to be with and I love the great outdoors and i love the seen. I like to play football and i like to go boating and i live to do all fun things. I love the movies and i like to go 4x4 wheeling. In my truck .
Eric
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.
Felipe
58 • Chicago, Illinois, United States
Seeking: Female 34 - 52
Kindness, Love, Fun, Adventure
I am a fun loving family man
DAVID
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
Abi
55 • Chicago, Illinois, United States
Seeking: Female 27 - 45
I AM SWEET, AMBITIOUS AND THOUGHTFUL
Love to Travel and like to meet people from different culture,
Curtis
58 • Chicago, Illinois, United States
Seeking: Female 33 - 52
Looking for love
Very charismatic individual love having fun
Charles
56 • Chicago, Illinois, United States
Seeking: Female 44 - 61
Looking for love
Hi. I am an empty nester and proud father of four amazing young adults. I am a new grandfather and I am very active and an extremely loyal partner. I was married for 23 years. Looking for my best friend and true partner.
Regis
55 • Chicago, Illinois, United States
Seeking: Female 20 - 35
Romance Start With A Conversation
I love traveling, Dining out, Having fun and enjoying life to the fullest...
Ola
53 • Chicago, Illinois, United States
Seeking: Female 29 - 49
Am a quite gentleman, easy going, go getter
Very caring , romantic, looking clean always fun to be with.love cooking as well.
Roberto
58 • Chicago, Illinois, United States
Seeking: Female 32 - 50
Looking for love 😘.
I am a retired attorney who lives in Chicago wants to travel with someone.
Tye
51 • Chicago, Illinois, United States
Seeking: Female
Let's Explore the Possibilities...
This knowledge will all come in time, but I am Affectionate, Loyal, Honest and Honorable and Just with Integrity. Caring with Compassion and Responsible with Accountability for starters.
michael
57 • Chicago, Illinois, United States
Seeking: Female 35 - 64
just looking for my last first kiss!
Soon to retire and would love to find someone to explore the world with.. It's sad I have to say this, but if you're wearing a mask in any of your pictures, I'm not interested
Sergio
51 • Chicago, Illinois, United States
Seeking: Female 25 - 60
Very friendly
Love being with someone who is outgoing
Sergio
51 • Chicago, Illinois, United States
Seeking: Female 25 - 60
Very friendly
Love being with someone who is outgoing
Sergio
51 • Chicago, Illinois, United States
Seeking: Female 25 - 60
Very friendly
Love being with someone who is outgoing
Sergio
51 • Chicago, Illinois, United States
Seeking: Female 25 - 60
Very friendly
Love being with someone who is outgoing
Manu
59 • Chicago, Illinois, United States
Seeking: Female 40 - 58
Happiness
Hard worker loyal willing to compromise
Morris
58 • Chicago, Illinois, United States
Seeking: Female 31 - 49
Hello all to new friends
I am not the best and nor the worst normal person enjoying the good things with good manners.
yasser
54 • Chicago, Illinois, United States
Seeking: Female 22 - 37
أبحث عن زوجه عربيه عمرها 25-37
I live in Chicago and work in business
Marcus
52 • Chicago, Illinois, United States
Seeking: Female 30 - 47
Looking for that special someone!
Confident and caring, good listener, supportive, outgoing.
edgar
53 • Chicago, Illinois, United States
Seeking: Female 20 - 35
seeking princess
I am a hard working man, have always been a great provider. I am seeking a new pretty thing to maybe start a new life with are you the one?
Thomas
53 • Chicago, Illinois, United States
Seeking: Female 24 - 32
Looking👀
Down to Earth
Eddie
58 • Chicago, Illinois, United States
Seeking: Female 30 - 45
seeking marriage
Hard working, loving and family oriented
Xlenn
53 • Chicago, Illinois, United States
Seeking: Female 33 - 55
Read my profile first then message me 😄
I'm 55 years old, active, biking, running and CrossFit, I love outdoor activities in summer or winter, play bass guitar, sketch artist and study Spanish language. Not traveling outside of USA because of COVID-19
Joe
51 • Chicago, Illinois, United States
Seeking: Female 20 - 48
All we need is love
I have everything but somebody to love
Paul
56 • Chicago, Illinois, United States
Seeking: Female 23 - 35
Love all woman
Easy going liove riding my motorcycle. Love going on vacations
Victor
54 • Chicago, Illinois, United States
Seeking: Female 27 - 44
Looking for true love
Hard working professional, loves family life. Loves travel, adventurous, loves the outdoors.
Donnie
57 • Chicago, Illinois, United States
Seeking: Female 21 - 47
x
enjoy travel
timothy
54 • Chicago, Illinois, United States
Seeking: Female 18 - 43
hi
later
David
53 • Chicago, Illinois, United States
Seeking: Female 19 - 45
Looking for love
I am a successful individual who is seeking my soul mate.
Greg
59 • Chicago, Illinois, United States
Seeking: Female 18 - 35
Just looking for my girl...
I'm a very sweet guy that is looking for a loyal partner to enjoy experiencing life with...is that you?
lance
56 • Chicago, Illinois, United States
Seeking: Female 18 - 40
looking for ms right
hardworking individual with a can-do sprite, whos' educated, a self-starter, intelligent, motivated person who strives to get ahead, and seeking all what life to offer.
NEW
Alonzo
52 • Chicago, Illinois, United States
Seeking: Female 29 - 50
Looking for the one
Wanting to spend time together

Next
first
Previous
Next
last