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
Filipino Dating

/

Single Men

/

United States

/

Illinois

/

Chicago

/

Over 50

36 - 70 of 100
Glenn
51 • Chicago, Illinois, United States
Seeking: Female 26 - 42
Looking for love!
I’m a sincere athletic guy that loves life and is looking for someone to enjoy it with.
Mark
54 • Chicago, Illinois, United States
Seeking: Female 26 - 41
Looking for a wife
I like to have fun in life enjoy the outdoors,traveling the family.
Mr Love to love
51 • Chicago, Illinois, United States
Seeking: Female 26 - 51
Looking for love and a True Partner
Single man look for my Mrs Love.
Cashell
55 • Chicago, Illinois, United States
Seeking: Female 20 - 36
Enjoying life and having fun
I love my job sometimes I work a lot hour I love sports I basketball Football Baseball Tennis and Hockey I love to workout I like to take walks I like to cook I like the movie I like to travel and I like to see people around me have fun I’m a big ted
Allen
57 • Chicago, Illinois, United States
Seeking: Female 29 - 47
I want to go back to Cebu ! Lapu Lapu city
I’m into swimming & walking .. listen , I’m quite not a tough guy … I’m into laughing joking you . I expect you to bring me around non violent people . I HATE Violence!! Come with me to funny white man .. 🙋🏼‍♂️🤓 thanks for reading 📖
Andy
52 • Chicago, Illinois, United States
Seeking: Female 18 - 55
Seeking friendship & Long-term relationship.
I am very ambitious, athletic, goal-oriented and full of humor. I love to make jokes and have fun. For we only have one life to live.
Rory
57 • Chicago, Illinois, United States
Seeking: Female 29 - 50
Looking for that special Lady
I am 57 Human Resouce Manger living and working in Chicago. I am looking to relocate to the Philippines within the next 2 years. I do not llike the cold so I am ready to leave here. I love to exercise and have lost over 200 pounds over the past 5 yea
Ron
51 • Chicago, Illinois, United States
Seeking: Female 18 - 24
USA GENTLEMAN SEEKS LOVING CARING PARTNER
SUCCESSFUL BUSINESSMAN WANTS LOVING PARTNER TO SHARE MY GOOD LIFE
Douglas
58 • Chicago, Illinois, United States
Seeking: Female 30 - 55
Hello, Joy, Passionate & honest, fun and energetic. I am at my 2nd home in Phoenix October 3-12
Joel
53 • Chicago, Illinois, United States
Seeking: Female 22 - 32
American Single Guy
Own and operate a hostel in downtown Chicago, Illinois, USA.
Jay
52 • Chicago, Illinois, United States
Seeking: Female 23 - 61
Hi
I'm a divorced investment banker who is looking for someone I can spend quality time with.
timothy
54 • Chicago, Illinois, United States
Seeking: Female 18 - 43
hi
later
Hitstick
59 • Chicago, Illinois, United States
Seeking: Female 31 - 51
Ass Eater Pussy Eater Toe Sucker Butthole Fucker
Love to PLEASE THE WOMAN before seeing that i get pleased,for the WOMAN (ALWAYS) CUMS 1st and 4 MOST
James
55 • Chicago, Illinois, United States
Seeking: Female 20 - 35
Looking a women 18 to 35 for marriage
I'm a responsible a good provider was a great husband and still is a good father, I'm a lover and I respect others
joe
53 • Chicago, Illinois, United States
Seeking: Female 26 - 36
Taking it one day at a time
52yo...175cm/75kg...Chicago USA... dark blonde/green eyes...likes healthy food and staying in shape...Hope to see you soon!
Rodney
55 • Chicago, Illinois, United States
Seeking: Female 27 - 46
I'm a serious man about things in life..
Life is short, don't need drama..
Michael
53 • Chicago, Illinois, United States
Seeking: Female 21 - 72
Looking For My Best Friend; Life mate
Am Poish and Jewish living in Chicago area with no children and have amazing cats. I am reliable, passionate, faithful, genuine, open minded. My step mom is a Filipina from a city outside of Cebu called Talamban but lives in Chicago area happily m
Michael
52 • Chicago, Illinois, United States
Seeking: Female 21 - 38
Hoping to find forever love
I'm a very easy going, laid back guy who only is here to find true love & to give my heart to someone.
Edgar
59 • Chicago, Illinois, United States
Seeking: Female 30 - 49
Edgar
Single man looking for a simple minded other half.
Mike
54 • Chicago, Illinois, United States
Seeking: Female 26 - 46
Looking for a companion to enjoy our life together
I enjoy travel, fine wine and dining, I enjoy cooking, sports and the outdoors. I prefer to play sports as opposed to watching.
Dylan
53 • Chicago, Illinois, United States
Seeking: Female 28 - 75
looking for my best friend soulmate
Polish and Jewish American living in Chicago area with no children and have 2 amazing boy cats seeking true unconditional love!
Bill
55 • Chicago, Illinois, United States
Seeking: Female 25 - 45
Seeking a smart and adventurous companion.
My interest is a serious, long term relationship. I am considering moving to SE Asia (Philippines ,Thailand, Malaysia) this year, and would like to find a someone to join me.
Tony
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.
EDGAR
51 • Chicago, Illinois, United States
Seeking: Female 23 - 37
LIFE IS SHORT SO LIVE IT TO THE FULLEST!
I am an in the Transportation business in the USA, I enjoy physical fitness , Hockey 🏒, Big Game Hunting, Saltwater Fishing, I am a private Pilot.
JB
57 • Chicago, Illinois, United States
Seeking: Female 29 - 49
Looking for something different
Semi retired. Lived in Asia for several years and looking to move back.
Paul
55 • Chicago, Illinois, United States
Seeking: Female 40 - 50
hi looking for my only one ..
I like camping, fishing , watching movies,going out to eat ,walks on the beach.
Vincent
54 • Chicago, Illinois, United States
Seeking: Female 28 - 55
TOP TEN REASONS TO DATE 
10. Because he's Italian and the Italians discovered America. (Well, that's what I heard) 9. Because he thinks it's cool tha
SEAN
55 • Chicago, Illinois, United States
Seeking: Female 29 - 47
I love life !
I’m a world traveler and a animal lover . I like sports and travel often to see my teams play in other cities . I’m looking for a wonderful , funny and beautiful lady to make my life complete .
Thierry Thompson
57 • Chicago, Illinois, United States
Seeking: Female 26 - 49
Chicago South Loop
Teacher
Ricky
51 • Chicago, Illinois, United States
Seeking: Female 27 - 45
Seek n Serenity
I'm seeking a place of peace and serenity. I will need help from a beautiful woman inside and out.
Rick
59 • Chicago, Illinois, United States
Seeking: Female 30 - 49
Kind handsome man
I am retiring to the Philippines in a few years, hope to visit there soon, I am a truck driver and musician I am kind and very caring person
Kevin
55 • Chicago, Illinois, United States
Seeking: Female 31 - 25
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 .
Tracey
54 • Chicago, Illinois, United States
Seeking: Female 28 - 47
Movie lover looking for his leading lady!
My name is Trace and if I had to pick three words to describe me they would be positive, a little shy, and someone who loves to entertain, laugh and have fun w/ family and friends. Okay, that was a few more than three words, but it’s fun to break the
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.
Marcus
53 • Chicago, Illinois, United States
Seeking: Female 30 - 47
Looking for that special someone!
Confident and caring, good listener, supportive, outgoing.

Next
first
Previous
Next
last