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

1 - 35 of 100
J
59 • Chicago, Illinois, United States
Seeking: Female 25 - 35
DON'T SETTLE
Smooth, easy going but driven to succeed at work and play. Strong work ethic. Drawn to the water. Like to travel and keep in shape spiritually, mentally and physically. I also like nice toys. 6'4 219lbs (at least today). Truly a unique individual
Christopher
59 • Chicago, Illinois, United States
Seeking: Female 33 - 42
Seeking Serious Relationship
I am from the midwestern United States and spent most of my career working overseas and have lived and worked in Latin America, Africa, and the Middle East as well as spent time in Asia and Europe. I returned to the U.S. five years ago and now work as an international business and trade consultant. My friends would describe me as intellectually curious with an enduring interest in other cultures, kind hearted, easy going with a willingness to laugh at myself, and an ironic sense of humor. I laugh easily and enjoy spending time with friends and family and meeting new people. For anyone who takes an analytical approach to determining compatibility,
Pat
56 • Chicago, Illinois, United States
Seeking: Female 42 - 59
I need a lover who won't drive me crazy
I am born 1966, I am 60 years of age. I cannot sing! I cannot dance! 50% I can make you laugh. Maybe you are crabby. I am allergic to cats, dogs, and drama. I have no apps. I can only chat here.
Vlad
58 • Chicago, Illinois, United States
Seeking: Female 38 - 46
let's live our lives happy together
I'm loyal, honest simple men. I like outdoors mainly anything close to the water, hiking, working out, bicycling, walking. I still believe when there is s spark between two people then both can make a relationship beautiful with unforgettable memorie
J
57 • Chicago, Illinois, United States
Seeking: Female 18 - 41
Finding joy in little moments and big flavors.
I’m unable to view or send messages. Thanks for checking out my profile! 😊 Guidelines: 🚫 No reply if: Your search age range is 18-99, you have only one picture, or your first message is just “Hi,” “Hello,” etc. (Let’s be more creative! 😅) 📱 No
John
55 • Chicago, Illinois, United States
Seeking: 23 - 53
American Ex Pat Seeking Companionship
I'm a Mature American recently repatriated after an exciting experience living overseas in the Philippines for over two years as a Digital Nomad. I'm looking for someone to share my free-spirited lifestyle with.
JD
57 • Chicago, Illinois, United States
Seeking: Female 18 - 35
Let's Video Call ;)
Hello, I'm an open-minded, active guy looking for a genuine connection. I like the simple things in life- family, friends, good conversation, good food, and laughing at misc funny stuff. I like simple things- dining out, trying different restaurant
Eli
51 • Chicago, Illinois, United States
Seeking: Female 18 - 25
I cannot be scammed, so don't even try!
Weighting over ten feet tall Feet of clay, head of gold Middle made of cannon balls Rumor has it swallowed whole Mineral, without a soul That's the story being told The estimated, undefeated Champion of the world Big yet unfamiliar Think bigger than the biggest bar Think big, that's only half as large Bigger, better, twice as hard Outsized, extra large Velocity very fast Bigger than the closest star Bigger than the motor car Quick, quiet, confident Comfortable, permanent Undisputed every tense Not a trace of what went left More equal than the best Unparalleled success Everybody Be impressed
Edwin
52 • Chicago, Illinois, United States
Seeking: Female 24 - 41
Greeting
I am 49 yrs old, born and raised in Chicago. I speak fluent English and Spanish. I am willing to learn Tagalog. Currently work in the transportation industry and study information technology during the nights and weekends. Faith is important to me a
Alex
59 • Chicago, Illinois, United States
Seeking: Female 22 - 52
Big guy, Big heart.
Oh boy, how do you put a whole lifetime in a little box ? I've experienced a little bit of everything, the highs and the lows. I enjoy the little things in life and look for some of those same qualities in other people. I'm attracted to people who ha
Michael
58 • Chicago, Illinois, United States
Seeking: Female 37 - 51
Seeking one special woman...
Hi! I'm on this site to try to find the perfect woman for me, so I'll never have to search again! 🥰 I'm kind and loving, and honest and sincere. I don't want to play games, and I'm serious about finding a relationship! I recently retired (😍) from an airline job, and I still get flight benefits (😍😍😍), so it's very easy for me to travel almost anytime. Now I'm looking for a new place to live - somewhere warmer, near the ocean... And I hope to find someone here who will be with me by my side for the rest of our lives. 🥰 Oh, one more thing - I have had a vasectomy, and I'm unable to make babies. So if you want more children, you should look for someone else... But if you don't want to ever have to worry about getting pregnant, then I'm your man! 😄😁
michael
59 • Chicago, Illinois, United States
Seeking: Female 35 - 60
looking to retire to the Philippines, a quite life
IF YOU'RE WEARING A MASK IN ANY OF YOUR PROFILE PICTURES....we're not compatible.. I know if you read my profile...... easy going guy, looking to retire to another country, I am duel citizen (USA & Germany), I love to travel, I love the country and people of the Philippines, I would love to have a filipina , I am young in heart, mind and body, no one ever believes my age
Mike
56 • Chicago, Illinois, United States
Seeking: Female 25 - 50
Enjoy the good life
I was flying helicopters in the South Pacific and heard a lot about the cuture from my mechanic. So, I'm planning to vacation in the Philippines in the next year and looking to meet wonderful people for friendship and hopefully more. Currently work gives me two weeks off every month, so travel is a must.
Patrick
59 • Chicago, Illinois, United States
Seeking: Female 21 - 60
Looking for the one for me
I am a happy kind person . I enjoy life ! I like sports and music, I play guitar. I work hard and enjoy my free time .I am not looking for someone young enough to be my daughter . If we are going to communicate I hope you can speak some English, I wi
Will
58 • Chicago, Illinois, United States
Seeking: Female 29 - 49
Peaceful Warrior from Birth
I was born in the southeast of the United States. I'm quiet until I get to know you, I enjoy cooking working out reading gardening my hobbies. I come from a Military Family on both sides, I am skilled in more than 50 styles of Martial Arts, Self Defe
Jesse
58 • Chicago, Illinois, United States
Seeking: Female 21 - 30
Smile 🤪 it's a New Day
Mature, respectful, hardworking Man with a sense of humor but yet serious. With high goals.average looking and smart 🤓. win win. you can't have everything, well maybe some do LOL. Anyways, I like to go for long walks, read a good book, go camping often, love the outdoors. swimming, biking. I eat healthy and exercise. I like to cook indoors and outdoors. I love dancing and try new things. I'm affectionate and like to treat a woman with respect and honestly.
Tim
56 • Chicago, Illinois, United States
Seeking: Female 25 - 50
Hello,Is It Me Your Looking For ?
Hello I’m a nice guy with a great sense of humor who is still searching for Mrs Right. Certainly not easy to find but I’m hoping to meet that one that I couldn’t live without. Love music,movies and would love to meet someone who is real and down to earth and can smile and have fun
tom
52 • Chicago, Illinois, United States
Seeking: Female 28 - 35
NO WHATSAPP!!! Stop asking!
Moving to a small village to be a water buffalo farmer is my dream, need a WIFE, need family. Orphaned I'm a young person at heart, mind and body. very active, Looking for a good women to be apart of my life and make a happy future together. I
John
58 • Chicago, Illinois, United States
Seeking: Female 18 - 32
The time has come:)
I am a genuine and caring person. I am physically fit, financially stable and emotionally mature. This year I am completing my Master's of Accounting full time and I am lucky that I can financially afford to do this. Family is very important to me and I enjoy learning about different people and cultures. I love to travel and make memories. I am caring, love to communicate and loyal. A one woman man. I am 100% single. Having gone through divorce I know how important it is to choose the right one and to not rush things.
Tony
59 • Chicago, Illinois, United States
Seeking: Female 26 - 40
Looking for a travel partner w/o kids!
I am looking to start a new life in a new land. I have travelled to almost twenty countries and would like to meet a partner who is willing to join me and see the rest. I plan to travel the world for a few years in order to learn the languages and cultures of different societies. I studied world history while at university and have an abiding admiration for the planet and its people. I seek a kindred spirit with whom to share the journey.
antonio
52 • Chicago, Illinois, United States
Seeking: Female 35 - 45
Looking for my perfect woman
Soy un hombre hecho a sí mismo que le encanta viajar y mirar hacia un día viven en la República Dominicana ... espero encontrar una mujer hermosa y atractiva que sabe ser leal y dedicado a su hombre ... SI NO SE EN BUSCA DE UN HOMBRE SUGAR DADDY O EN
Lamonte
54 • Chicago, Illinois, United States
Seeking: Female 25 - 50
Looking for someone honest 
I am looking for someone with honesty and integrity. Please be who you say you are–please no game players! We all wish we looked and felt the way we did 10 years ago! :) So don't send take pictures if asked. A person with a good sense of humor… 
Rafi
59 • Chicago, Illinois, United States
Seeking: Female 35 - 52
Rafi
I am a man of faith, a creature, true to myself and others, consistent with my convictions, flexible, easy, calm in dealing with various issues, ideas and circumstances. I love respectful acquaintance and friendship, I don’t like the arrogant, arrogant, arrogant, foolish woman, and I’m alienated from the moody woman. I am a person who loves life in its simplicity, loves nature with its beauty, loves friendship with its purity, loves loyal friends. I love joy and extroversion, I love temperance and banter, I love calm and serenity, I love traveling, it gives me positive energy.
Otis
52 • Chicago, Illinois, United States
Seeking: Female 34 - 38
JustOne
I'm just a hardworking guy looking for some happiness. I know you will want to know more, but I will go into complete detail when we speak to each other. I will say that I'm not on this cite looking for someone to live with. I'm looking for that special someone I cannot see myself without. I come from a very big family. We have had reunions every two years since 1991. I want to finally bring my significant other with me. This is why I am on this particular cite. True happiness and prosperity knows no color or nationality.
Cashell
58 • 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
Andy
54 • 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.
Joel
56 • Chicago, Illinois, United States
Seeking: Female 22 - 32
American Single Guy
Own and operate a hostel in downtown Chicago, Illinois, USA.
Jay
56 • Chicago, Illinois, United States
Seeking: Female 40 - 65
Hi
I'm a divorced investment banker who is looking for someone I can spend quality time with.
Alexander
55 • Chicago, Illinois, United States
Seeking: Female 30 - 70
Greg
52 • Chicago, Illinois, United States
Seeking: Female 35 - 60
A loyal , grounded man of good intentions.
Single no children, no drama. Hard working and creative.
lawrence
56 • Chicago, Illinois, United States
Seeking: Female 28 - 61
Slyvester
52 • Chicago, Illinois, United States
Seeking: Female 28 - 55
Robert
56 • Chicago, Illinois, United States
Seeking: Female 25 - 38
Very well educated Engineer seeking a relationship
Philosophical fun-loving world traveler
h
51 • Chicago, Illinois, United States
Seeking: Female 22 - 22
JohnnyV
51 • Chicago, Illinois, United States
Seeking: Female 30 - 49
Aye there, time for new beginnings. In search of t...
I am 6', -190 lbs, athletic build. I enjoy good eating, traveling, comedy, horror movies, grunge music, techno, rock, outdoors, beaches, Asian and Italian food, and if course spending time for the one that will complete me.

Next
first
Previous
Next
last