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

1 - 35 of 100
Tom
58 • Chicago, Illinois, United States
Seeking: Female 29 - 49
DON'T CONTACT ME IF YOUR PROFILE IS NOT COMPLETED...
Hello, I live in Chicago, USA. I'm loyal and honest person, financially stable, own a house and business, don't have any debts. I grew up in Poland, moved to USA long time ago, have dual citizenship 🇺🇸 and 🇪🇺 No addictions, I've been trying to live healthy life, eating healthy, no drugs or cigarettes I like sport's and traveling. I'm rather in for long relationship than in to fast marriage Yes, I like beauty in women, but I won't ask for any indecent pictures.
nino
51 • Chicago, Illinois, United States
Seeking: Female 20 - 42
Hi..
To describe you is to describe myself. You are rare and you know it. You do not settle for anything less than your best, and this reflects in the friends you choose, your dreams and aspirations and the quality of your life. We have discovered that "beauty, god, and haven" are states of the mind not places or things. But we can not seem to find our rare and uique soul-mate to share our life experinence with. Einstein said "i want to know god, everything else is just details". These are my details I am a man.
Dali
51 • Chicago, Illinois, United States
Seeking: Female 25 - 45
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.
Karl
59 • Chicago, Illinois, United States
Seeking: Female 18 - 39
Seeking For MARRIAGE !
I am a very laid back Black Male, trustworthy, honest, articulate, friendly, ect. I am looking for a nice you lady, to become PEN PALS with, and if it were to lead to more (marriage) than a friendship, that would be GREAT. So ladies send me a message, and lets chat.
Bruce
57 • Chicago, Illinois, United States
Seeking: Female 23 - 48
Praying for a special little miracle. . .
Well, I am very loving, caring, and affectionate. I am highly intelligent, good-hearted, and generous with my love. I have a good career in the technology field and perhaps have focused too much on my work in the last few years. I have realized that i have to find a woman to be with. I need that sweetness and kindness in my life. To the ladies who have written me. I will try to write back tomorrow. Thank you for your letters!!!
Will
56 • Chicago, Illinois, United States
Seeking: Female 26 - 44
Looking for a Long Term Relationship
I’m from Chicago in the United States. I recently visited the Philippines and fell in love with the country and the people. I’m looking for someone special that will hopefully turn into marriage. I’m able to travel often but it would be important for my partner to eventually relocate to the United States. I’m able to spend extended time in the Philippines. I’m not here to waste anyone’s time but to find forever true love. I’m a very compassionate person and care about people. I am thoughtful, genuine and sincere.
Alejandro
57 • Chicago, Illinois, United States
Seeking: Female 53 - 58
Vivo en Chicago Soy Ingeniero de Sistemas
Hablo 4 idiomas. Me encanta cocinar comida internacional Vivo a las afueras de Chicago Quiero jubilarme en 6 anos y vivir en la peninsula en mi amado Ecuador. Me encanta la cultura Europea, pues vivi alla por mas de 12 anos, y quiero viajar.
American
55 • Chicago, Illinois, United States
Seeking: Female 50 - 59
Let's heal the world together
% all natural man, no artificial preservatives, vegetarian friendly and kosher certified. A delicious blend of wholesome personality and fun, recommended daily supplement to reduce high blood pressure and stress. Ladies, please don`t misunderstand
JD
56 • Chicago, Illinois, United States
Seeking: Female 18 - 40
Marriage-minded
Hello, I'm an open-minded, active, genuine guy looking for marriage. I like the simple things in life- family, friends, good conversation, and laughing at misc funny stuff. I like simple things- dining out, trying different restaurants- but try to keep it healthy, movies, walks along the lake, rollerblading, most sports, festivals, road trips, traveling, etc. etc. Let's chat sometime and share more about each other ;)
Alex
56 • Chicago, Illinois, United States
Seeking: Female 22 - 48
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 have inner happiness and sometimes think of others before themselves. I too am a very caring person with a big heart. My friends know I will always be there for them and they can trust me with their life. I usually walk around with a smile on my face, full of personality and easily make other people smile, laugh. I'm very attracted to Asian women. I don't think I will be going to Asia anytime soon, so this is the next best thing. I've had some relationships, including with Asian women but I am single now and if I find the right woman here I will cherish her and take care of her. Hopefully forever.
Sal
58 • Chicago, Illinois, United States
Seeking: Female 40 - 59
"Is there a part of me, that's a part of you? "
To my future heart, if you are out there. Please accompany me on an epic road trip on a cool breezy night with the fall moon just above the horizon the air filled with Ocean Mist, driving aimlessly down the Pacific Coast Highway in an old Lincoln convertible. As we drive with no particular place to go, we watch the waves return from a long night out at sea, enjoying each other’s company in long drawn out conversation filled with laughter and hope, while listening to “Peace Piece” ( Bill Evans) in the background as it fills the midnight air… So the story begins
Keith
52 • Chicago, Illinois, United States
Seeking: Female 21 - 36
Love the Life you Live
Hello! Thank you for viewing my profile. I'm single and own a very nice home in Chicago, Illinois, USA. The most important things in my life are faith, family and friends. I have two college degrees in Communications and Political Science, and I'm fortunate to enjoy a great career in professional sports. I enjoy traveling around the world, dining out, playing golf and spending time with family and close friends. I also enjoy movies, concerts and cultural events, along with quiet nights at home.
Tio gold
55 • Chicago, Illinois, United States
Seeking: Female 20 - 40
It is not the mountain we conquer but ourselves
Looking for a special lady who wants serious relationship leading to marriage. I'm tall dark and handsome .wonderful sense of humor .I'm very outgoing, hard worker and loyal ,passionate man.no kids.if you are for scams,western union or 🐂💩  save both our time .I look for someone stable ,and want to share life together
Eric
54 • Chicago, Illinois, United States
Seeking: Female 38 - 55
American Man Seeking A Serious Relationship
I am compassionate, driven, not hard on the eyes, and am told that I'm funny, sometimes even at the right moment. Calm, intellectual and still kind of a goofball. I'm 6'2" and weigh in at 215 pounds. I am educated, employed and try to enjoy life. ENTP personality type. I'm loyal, honest and trustworthy, and expect the same. I'm not here for games or wasting anyone's time.
Over
54 • Chicago, Illinois, United States
Seeking: Female 40 - 52
WILL ONLY MEET IN PERSON IN CHICAGO AREA
If you like your partner to be educated, intelligent, mature, easy-going, witty, affectionate, honest, romantic and a great lover, well, what are you waiting for then? Due to lots of scammers on this site I am removing my pictures so that I have less contact from them however if you have patience you will view my pictures at the same time that you also need to provide them so that I know you are the same person too.
Edriss
56 • Chicago, Illinois, United States
Seeking: Female 30 - 52
Head, Hands, & Heart Available for Miss RIGHT
1) If you don't have a profile pic, 2) if you have any children, or 3) any cats, 4) are a conservative or follower of that 45th fake president, - any or all of the above, Please move on and don't msg, or fave me. You will not be "The One" to change m
Aaron
59 • Chicago, Illinois, United States
Seeking: Female 30 - 48
Hello from chicago
Hi, thank you for checking out my profile, I guess you could say I am the tall athletic type, in my mid 50s stable employment, decided to reach out and entertain the crazy idea of meeting a woman from someplace that is so different than where I a
Ricky
59 • Chicago, Illinois, United States
Seeking: Female 25 - 45
If you can't do a live video, 📷 please keep movin
I am caring and a loving man.I am Honest, and enjoy boating and traveling in the Oceans & Lake. I love fishing and riding jet-skis, going to the movie and plays. I enjoy playing basketball, swimming, football. i love setting up different business.
Sam
52 • Chicago, Illinois, United States
Seeking: Female 29 - 45
Seek life partner and happy family :)
Hi. I'm a nice, family oriented guy, and I seek my special partner. I have many goals, but I like to relax in my free time. I enjoy simple pleasures the most--cafes, conversations, friendships, good films, and travel. I have a creativity, intellect, and a good sense of humor. I am caring, affectionate, and friendly. I hope to find a kind hearted, attractive woman to build a family and enjoy life with. I like kids and welcome yours :)
Yisrael
52 • Chicago, Illinois, United States
Seeking: Female 25 - 58
Seeking real love and marriage
Shalom and Asaalam My name is Yisrael I'm Cuban from Chicago I'm kind,honest, healthy, caring,trustworthy,understanding,respectful, compassionate,romantic,loving, very affectionate,thankful,thoughtful I like to everything in action.I'm passionate I study Judaism and Sufi. I'm hard working,I'm simple and live simple I seek marriage real love no games here pls serious reply only is seeking marriage and real and respect. I'm very spiritual have sense of humor I don't care what ages but only important is modesty, respect,personality,spiritual,creator fearing I like to hold hands, cares, kiss, I'm very affectionate .pls serious reply only to reach. S.K.y William.savigne I'm healthy eat healthy very spiritual I'm openminded.I'm thankful,and thoughtful person I don't care about luxury and don't care material what's important spiritual, heart,and soul, simple ,respectful ,modesty, respect kindness,humbles, and appreciate life what the creator Allah ,YAHVEH has given us everything is a blessing .
Hector
57 • Chicago, Illinois, United States
Seeking: Female 25 - 42
loyal,friendly who is looking for a serious girl
I'm healthy I work out at the gym I like to go out and enjoy the weather and the ocean. I like to travel, watch movies and cook. I'm learning Vietnamese. . sk*pe,hector.rodriguez705Tôi thích đi ra ngoài và vui chơi với bạn bè và gia đình. Tôi thích đi cắm trại, đi du lịch, nấu ăn và chỉ mất một đi bộ trên bãi biển.
金在光
53 • Chicago, Illinois, United States
Seeking: Female 48 - 65
Alirio
54 • Chicago, Illinois, United States
Seeking: Female 32 - 54
Chauncey
57 • Chicago, Illinois, United States
Seeking: Female 30 - 50
Real Man looking for love
I'm a hard working man,college student, athletic love running ,cooking ,sports and working ,making new friends and I'm a one woman man.I don't want to be on this dating site forever.Thank you!
Siraj
52 • Chicago, Illinois, United States
Seeking: Female 26 - 44
IF YOU ARE NOT A US CITIZEN PLEASE DO NOT RESPOND
On here looking to establish a relationship with someone.
Tim
54 • Chicago, Illinois, United States
Seeking: Female 30 - 60
I am a very loving. passionate and affectionate. ...
Loving, gentlemen, passionate and affectionate.
Ron
51 • Chicago, Illinois, United States
Seeking: Female 18 - 29
USA GENTLEMAN SEEKS LOVING CARING PARTNER
SUCCESSFUL BUSINESSMAN WANTS LOVING PARTNER TO SHARE MY GOOD LIFE
Mell
55 • Chicago, Illinois, United States
Seeking: Female 35 - 46
Robin
55 • Chicago, Illinois, United States
Seeking: Female 20 - 41
Puerto rican currently living in chicago, I enjoy...
Sanjay
58 • Chicago, Illinois, United States
Seeking: Female 18 - 65
Mario
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
Frederick
52 • Chicago, Illinois, United States
Seeking: Female 18 - 52
Looking for locals
Tall, athletic professional
Mustafa
54 • Chicago, Illinois, United States
Seeking: Female 32 - 50
A kind and respectful type of person.....
Looking for a life partner
Edgar
59 • Chicago, Illinois, United States
Seeking: Female 30 - 49
Edgar
Single man looking for a simple minded other half.
Nardo
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.

Next
first
Previous
Next
last