Mature dating in Chicago

Generations Dating - The online dating site for older singles looking for fun, friendship or serious relationships.

Senior singles looking for lasting relationships in The United States

At Generations Dating we specialise is connecting older members with people they actually might want to meet. All of our members are over 40 and looking for someone of a similar age so you will feel right at home.

Join for free today and start searching our extensive database of mature singles in Chicago and anywhere else in The United States.

How do you know what dating site is the right one for you?

This is a difficult question and very much down to personal preference. Some people prefer the convenience of mobile dating app's while others like a more personalised experience. What we can say for sure is that if you are over 50, its proven that dedicated sites for mature members generally have a better success rate than the more general online dating websites.

Find singles over 40 in Chicago today

Secure and anonymous, Generations Dating allows members to search and view members nearby with ease. Communication is kept within the site so there is no need to give out potentially personally identifiable information.

We offer a live help feature so you can get support from a real person whenever you need it and even offer an optional photo verification service so you know the persona you are speaking with is genuine, look out for the green tick in the corner of a photo.


Register for free Create your own dating profile and connect with other mature singles looking for love and romance.
Simple matching Finding compatible members is fast and easy. Get daily suggestions
Connect via built in communications tools Our secure messaging systems means you can keep your personal contact information private
New members every day Lots of new members registering every day gives you a great chance to meet someone special

Tell us something about yourself

Tell us a little about yourself and let our advanced matching system suggest potentially suitable partners nearby or dive right in and browse singles near Chicago who might catch your eye. Once you are registered you can view members who are online when you are so you can get the conversation started. Don't worry if you are a bit shy, why not send them an icebreaker or a cheeky wink to let them know you are interested. Remember to add a photo. You will receive far more interest with a recent photo.

All you need is an open mind and a working email address to get started. Create your free account by completing the fast registration form above to begin browsing mature members today.

Safe and secure

In order to protect our members privacy we use the latest encryption, scamalytics and a team of real people who monitor the site for suspicious behaviour. All your communications can be done via the secure site so there is no need to give out potentially personally identifiable information and we never display your personal details on the site for other members to see.

Don’t wait any longer, sign up today.