Login

Chicago Men Interested in Penpals

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

/

Penpals

/

Location

/

Illinois

/

Chicago

36 - 70 of 100
Brian
47 • Chicago, Illinois, United States
Seeking: Female 18 - 30
Adventurous and Respectful
Hello, I'm an honest and good guy. I like staying healthy: going to the gym and eating healthy. Also enjoy having campfires, going for walks, visiting the beach, snorkeling, and learning about almost everything. I don't go to the bar, smoke, gambl
Jason
66 • Chicago, Illinois, United States
Seeking: Female 37 - 58
Forever more
Retired lawyer college professor. Married to lovely woman over 20 years and we just grew apart. And had a really cool child. Im fun, intelligent, empathetic, original and creative.
jaime gradilla
29 • Chicago, Illinois, United States
Seeking: Female 18 - 36
Bigmann
61 • Chicago, Illinois, United States
Seeking: Female 40 - 60
Am seeking 1 mature woman with traditional values.
I am a single 60 year old Black American that is 6'2" tall, 210 pounds, single and do not have any children. I have retired from the military as an officer and am currently working as a Director of Human Resources with another major corporation. I love sports, exercising, running, billiards, golf, bowling, outdoor activities, movies, concerts, festivals, beach, traveling, and eating good food. I love to have fun and laugh. I do not know how to sing but can try to dance, LOL. I am a loving committed individual that believes love should be given at 100% and received the same. My goal is to visit the Philippines for the first time to meet my life partner. After the initial meeting, we will make plans for my relocation and retirement to the Philippines in order to be with my life partner forever.
Daniel
51 • Chicago, Illinois, United States
Seeking: Female 35 - 53
Looking for a strong connection
I’m an energetic, curious, passionate, and creative soul who is continuously stimulated by deep and significant connection. By day I’m a business executive, author, and speaker, and one who looks to find the meaning in every moment. By night I am int
Erik
48 • Chicago, Illinois, United States
Seeking: Female 19 - 43
Looking for something real and honest. Love and f...
Traveled and adventurous. I love my family and life experiences. I am an avid runner and into rock climbing and boxing.
Alejandro
34 • Chicago, Illinois, United States
Seeking: Female 28 - 38
animated homebody getting some genuine fresh air
I'm really simple, I go to work and come home, really hard to break the habit, I live in the city but I'm anti social for no reason just a force of habit, really trting to turn that around , life is fun and full of wonder i cant share life if im home
Andy
40 • Chicago, Illinois, United States
Seeking: Female 19 - 23
Searching for my future wife
I'm 39 years young. I'm very active and like to explore surrounding areas.. I like to travel ... I'm really spontaneously and I'm having always a smile with me
Manny
39 • Chicago, Illinois, United States
Seeking: Female 25 - 29
Great God fearing man who loves to laugh.
I’m an artist, muralist, lover of God good music , art and travel.
Cory
34 • Chicago, Illinois, United States
Seeking: Female 23 - 29
I’m cory
I workout a lot! I’m muscular. I’m in sales! Ima territory manager. I have some education as well! I’m looking for a longterm relationship!
Roman
41 • Chicago, Illinois, United States
Seeking: Female 21 - 30
Looking for a pretty thing to complete me
I’m single and have no kids. I’m 5’11, 190lbs I’m fit and live a healthy lifestyle. Love traveling, but also a home body. I don’t like bars and clubs. I like staying at home Netflix and chill.
Ferdinand
26 • Chicago, Illinois, United States
Seeking: Female 18 - 35
Billy
48 • Chicago, Illinois, United States
Seeking: Female 25 - 42
Looking for my angel!! I hope it's you🪷🥰
Funny. Handsome. Honest. Inspiring. Creative. Im very spiritual and have a strong connection with God. Doing my best everyday to continue to become the best man I can be! Very active, fit, and healthy. I've been to the Philippines 3 times and hopeful
Andre
52 • Chicago, Illinois, United States
Seeking: Female 21 - 40
Sincere, honest, loyal, intelligent real man
Civil Engineer/IT Consultant Successful businessman and kingdom-oriented follower of Jesus Christ
Mark
33 • Chicago, Illinois, United States
Seeking: Female 18 - 22
Hey hey
Hardworking single father - looking for a partner
Ken
62 • Chicago, Illinois, United States
Seeking: Female 35 - 45
Handsome, Very Romantic Man!!!
God Loving, family oriented, Romantic, funny 😁, love to travel etc
Terrell
41 • Chicago, Illinois, United States
Seeking: Female 22 - 39
Humble and blessed
Love living life and family. Goal orientated just need that special person to enjoy life with.
Mike
56 • 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.
sam
43 • Chicago, Illinois, United States
Seeking: Female 23 - 40
Eat, play, love, and adore.
Hopeless romantic 💔
Carmelo
48 • Chicago, Illinois, United States
Seeking: Female 18 - 46
let's keep this incog, lol
Dylan
55 • 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!
Stanley
33 • Chicago, Illinois, United States
Seeking: Female 20 - 30
Ben
28 • Chicago, Illinois, United States
Seeking: Female 20 - 30
Hello
Passionate about music, work in sales. Not much more to it.
Stephen
37 • Chicago, Illinois, United States
Seeking: Female 21 - 39
Hello!
I work in film and television. I love cooking and playing guitar
frederick
62 • Chicago, Illinois, United States
Seeking: Female 47 - 64
Positive influence
Love classical music; play chess; had a stoke, left side affected. Love to: cook; waters activities; Own and operates finance firm. 5 grown children, 4 boys, all attended college.
JB
59 • 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.
Daniel
32 • Chicago, Illinois, United States
Seeking: Female 27 - 48
LookingHoping
Have traveled a lot, enjoy new places, foods, and people; read a lot; enjoy most music.
Raphael
52 • Chicago, Illinois, United States
Seeking: Female 27 - 45
Looking for Friendship and maybe a Relationship!!!
I am a single man who lives in a major city in the USA. My last relationship ended right before COVID, and I have been single since. I do have children, but they are grown. I have BS and MS degrees and have a professional career.
Jason
41 • Chicago, Illinois, United States
Seeking: Female 22 - 39
Chivalrous gentleman
Hey there. Jason here. Hard working guy. Building my way to the top and I am looking for my soulmate. I'll put more in when I have time, busy at work.
Thierry Thompson
60 • Chicago, Illinois, United States
Seeking: Female 26 - 49
Chicago South Loop
Teacher
Bryant
52 • Chicago, Illinois, United States
Seeking: Female 25 - 43
No scammers. I will make you verify you are real.
I'm a fun loving guy that likes to have a good time.
Ryan
33 • Chicago, Illinois, United States
Seeking: Female 20 - 99
Ask me
Jason
41 • Chicago, Illinois, United States
Seeking: Female 18 - 21
Pokpok and cheap girls need not apply
Find out for yourself
Dan
41 • Chicago, Illinois, United States
Seeking: Female 18 - 30
Date to marry
I am adventurous and if I start sending you a message hopefully you will piece it together with the next two messages I send you.
Sean
63 • Chicago, Illinois, United States
Seeking: Female 18 - 55
A man in a field of snowflakes
I am easy going and looking to eliminate the trappings of a normal life and looking forward to seeing as much as life has to offer.

Next
first
Previous
Next
last