11 Senior Dating Tips To Empower Your Fresh Start

Life is full of chapters, each with its own unique adventures. If you find yourself single and ready to mingle, it’s time to embrace the excitement of dating again. The dating landscape may have changed since you last explored it, but the thrill of connection remains the same.

This is your chance to rewrite your love story, create new memories, and forge meaningful relationships. Dating isn’t just about finding a partner; it’s a wonderful source of joy, companionship, and personal growth. It’s a chance to meet people, try new activities, and reignite your passion for life.

So, take a deep breath, step outside your comfort zone, and let yourself be swept away by the possibilities that await you. This is your time to shine!

Why Date?
It’s More Than Just Romance

Beyond the butterflies and candlelit dinners, dating offers a wealth of benefits for your overall well-being:

  • Companionship: Sharing laughter, conversation, and experiences with someone special can combat feelings of loneliness and isolation.
  • Increased confidence: Putting yourself out there and making connections can boost your self-esteem and sense of self-worth.
  • Personal growth: Dating encourages you to step outside your comfort zone, try new things, and learn more about yourself and others.
  • Stress reduction: Spending time with someone you enjoy can lower stress levels and improve your mood.
  • Mental stimulation: Engaging conversations and shared activities can keep your mind sharp and active.
  • Expanded social circle: Dating often leads to meeting new friends and expanding your social network.
  • Fun and adventure: Dating later in life can provide excitement and spontaneity into your life, opening doors to new experiences and adventures.

Keep in mind that dating isn’t just about finding “the one” (though that’s certainly a possibility!). It’s about enriching your life, expanding your horizons, and discovering new sources of happiness.

11 Practical Dating Tips for Seniors

Dating as an older adult can be an exciting new chapter! Whether you’re re-entering the dating scene after a long hiatus or simply looking to meet new people, it’s important to approach dating with confidence and a bit of know-how.

Here are 11 practical senior dating tips to help you navigate the modern dating landscape and increase your chances of finding meaningful connections:

1. Be Your Authentic Self

Whether you’re crafting an online dating profile or chatting with someone in person, authenticity is key. Showcase your true personality, interests, and values. Don’t try to be someone you’re not; the right person will appreciate you for the incredible individual you are.

2. Strike Up Conversations

Initiating conversations can be intimidating, but remember, everyone feels a little nervous at first. Ask open-ended questions, and show genuine interest in the other person. You might be surprised at how easy it is to connect with someone once you start chatting.

3. Prioritize Safety

Your safety is paramount. If you’re meeting someone online, choose a public place for your first date, let a friend or family member know where you’re going, and trust your instincts. If something feels off, don’t hesitate to end the date early.

When dating online, be cautious about sharing personal information too soon and report any suspicious behavior.

4. Be Patient and Open-Minded

Finding the right person takes time. Keep going even if you don’t meet your perfect match right away. Be open to different types of people and experiences. You might be surprised at who you connect with.

5. Set Realistic Expectations

Remember, no one is perfect. Everyone has flaws and baggage. Focus on finding someone whose values, interests, and personality align with yours, rather than seeking perfection.

6. Communicate Openly and Honestly

Good communication is the foundation of any successful relationship. Share your thoughts, feelings, and expectations with your date. Listen actively to what they have to say. Be respectful, even if you disagree.

7. Have Fun and Enjoy the Journey

Dating should be enjoyable, not stressful. Don’t put too much pressure on yourself to find “the one.” Relax, have fun, and embrace the experience. You never know what adventures or connections await you.

8. Honor Your Past, Welcome Your Future

If you’ve experienced loss, dating again can be a way to honor your past while embracing new possibilities. Allow yourself to heal and move forward at your own pace. Remember, opening your heart to new love doesn’t diminish the love you shared with your previous partner.

9. Celebrate Differences

It’s perfectly normal to date someone who’s in a different stage of life. Embrace the diversity of experiences and perspectives, and focus on finding common ground and shared interests. Open communication and mutual respect are key to navigating these differences.

10. Make Choices That Are Healthy and Fulfilling

Prioritize your own well-being. Choose partners who respect and support your needs. Engage in activities that bring you joy and fulfillment. Remember, your happiness is important.

11. Embrace Your Independence

There’s absolutely nothing wrong with being single. If you’re not ready to start dating, that’s perfectly okay. Focus on your own happiness, pursue your passions, and enjoy the freedom that comes with being single.

Explore Your Options

Ready to dip your toes back into the dating pool? Whether you’re a seasoned dater or new to the scene, there are numerous ways to connect with potential partners. Here are some options to consider:

Online Dating Apps and Websites

  • SilverSingles: A popular platform specifically designed for single seniors, emphasizing personality compatibility and shared interests.
  • OurTime: A vibrant community for singles over 50, offering various ways to connect, from virtual events to in-person meetups.
  • Bumble: This app empowers women by letting them initiate the first move, creating a more balanced and respectful dating environment.
  • EliteSingles: A platform that attracts educated and career-oriented individuals using a personality test to match compatible partners.
  • Stitch: A community focused on companionship and shared experiences, offering group activities and events alongside traditional dating features.

Offline Meeting Spots

  • Senior centers: These community hubs offer a variety of activities, classes, and social events where you can meet new people and make friends.
  • Volunteer organizations: Giving back to your community is a rewarding way to connect with others who share your values and interests.
  • Social clubs and groups: Join clubs focused on hobbies like hiking, book discussions, or travel to meet people with similar passions.
  • Lifelong learning classes: Learn a new skill or pursue a hobby while meeting new people in a fun and relaxed environment.
  • Cultural events: Attend concerts, lectures, or festivals to connect with others who share your cultural interests.

The key is to choose an approach that aligns with your personality and preferences. Don’t be afraid to step outside your comfort zone and try new things. The most important thing is to have fun and enjoy the journey.

Finding Companionship at Any Age

Dating as a senior is an exciting journey filled with possibilities. By embracing this new chapter with confidence, openness, and a touch of wisdom, you can create meaningful connections and enrich your life in countless ways.

Remember, there’s no one-size-fits-all approach to dating. The most important thing is to be yourself, have fun, and enjoy the process of getting to know new people. Whether you find love, friendship, or simply a renewed sense of self, the experience of dating can be truly rewarding.

Discover a Community Built on Connection at The Clare

Here at The Clare, connections are more than just conversations – they’re the heart of our vibrant community. From shared meals in our elegant dining room to dynamic discussions in our cozy lounges, every corner of our community is designed to foster genuine connections and spark meaningful relationships.

If you’re ready to embrace a lifestyle filled with friendship, joy, and endless possibilities, contact us today to learn more and schedule a tour. We can’t wait to meet you!

LET'S CONNECT

Schedule a personal visit with our team to talk through your options and ask any questions you have. We're here to talk whenever you need us.

Executive Director
Monica Rusboldt, Executive Director at The Clare in Chicago, IL

Executive Director

Monica Rusboldt

Monica Rusboldt became Executive Director of The Clare in September 2022 and most recently held the position of Associate Executive Director. She completed her bachelor's degree in psychology with a minor in Spanish and business at Indiana University. She completed her Master of Science degree in occupational therapy at Rush University Medical Center in Chicago. Monica began her career at Northwestern Memorial Hospital, where she worked as an occupational therapist and was promoted to senior therapist. She joined The Clare in 2012, working as an occupational therapist, rehab director and eventually area director, managing multiple sites. She joined LCS® as the administrator in December 2019.

Monica is from Michigan City, IN and enjoys going back home to visit her family and friends. She lives in the Gold Coast and enjoys trying new restaurants, baking and traveling. She also enjoys yoga and reading.

Associate Executive Director/Director of Dining Services
Francesco Tardio, Director of Dining Services at The Clare senior living community in Chicago

Associate Executive Director/Director of Dining Services

Francesco Tardio

As our Associate Executive Director/Director of Dining Services at The Clare, Francesco Tardio oversees the community's comprehensive food and beverage operations while supporting community operations to enhance the experience for all residents and team members alike.

His background includes positions as food and beverage director, director of outlets and general manager for exclusive private clubs, hotels and restaurants in Chicago and the surrounding suburbs. Francesco holds a bachelor's degree in anthropology from the University of Illinois at Chicago and a master's degree in healthcare administration from Concordia University Chicago.

Healthcare Administrator

Healthcare Administrator

Liza Steinfeld

Liza joined The Clare in October 2022 as Administrator for The Terraces. Liza is a Licensed Nursing Home Administrator (LNHA) and Clinical Social Worker (LCSW) with a broad spectrum of work experience. She has held medical social worker positions in various Chicago hospitals and worked in Cambodia, Ecuador and the UK. Liza graduated from Cornell University, where she received her Bachelor of Science in Hotel Administration and earned her Master of Social Work at New York University.

Liza is a curious, lifelong learner, recently earning the designations of QAPI Certified Professional (QCP) and Dementia Care Specialist. She also has a bit of an adventurous streak and has enjoyed traveling to Guatemala and Gabon (Central Africa) in the last five years. When Liza is not planning her next trip, she enjoys doing crossword puzzles and abstract art. Liza is passionate about assisting at-risk populations, particularly older adults, and is excited to be part of a team dedicated to high-quality care.

Area Director of Finance
Dan Rogers, accounting expert supporting operations at The Clare in Chicago

Area Director of Finance

Dan Rogers

Dan Rogers has been with The Clare since 2011. He oversees the accounting team in the day-to-day operations of payroll, billing and accounts payable. He also prepares the monthly financials, works with management on developing annual budgets, projects future operating performance and coordinates necessary financial audits. He earned a bachelor’s degree in accounting from the University of Illinois at Urbana-Champaign and is a Certified Public Accountant.

Dan has been married since 2009 and has four kids. He is also a sports fan who especially enjoys college sports (Go Illini!), and is probably one of the very few people who roots for both the Green Bay Packers and Chicago Cubs. Outside of sports, Dan is an avid music fan.

Director of Sales & Marketing
Lynne Lukas, Director of Sales and Marketing at The Clare senior living community in Chicago

Director of Sales & Marketing

Lynne Lukas

As Director of Sales and Marketing, Lynne Lukas is responsible for planning, developing and directing all aspects of selling and marketing The Clare’s independent living, assisted living and memory care residences. She oversees sales, lead generation, referral development, advertising, strategic market planning and events as well as managing her department’s team. Before beginning her career in senior housing, Lynne was employed with a luxury hotel group in Chicago. She feels her hospitality background serves her well in her chosen profession.

Lynne resides on the north side of Chicago with her husband, David.

Senior Residency Counselor
Senior living expert Cathy Milano guiding new residents at The Clare, Chicago

Senior Residency Counselor

Cathy Milano

As Senior Residency Counselor at The Clare, Cathy is often the first point of contact for prospective residents, bringing a wealth of experience across all levels of retirement living and senior services. With over fifteen years in the senior living industry—and a dedicated tenure at The Clare since 2014—Cathy is deeply committed to helping residents find the right fit for their needs. Prior to her work in senior living, Cathy built a successful 20-year career in the financial sector.

Residing just northwest of Chicago, Cathy enjoys life with her husband, Mark, and their dog, Scarlet. In her free time, she loves visiting with her granddaughter, golfing, and unwinding at their cabin in Northern Wisconsin.

Director of Environmental Services

Director of Environmental Services

Lindsay Bailey

As Director of Environmental Services at The Clare, Lindsay leads Environmental Services with a focus on modernizing operations, building high-performing teams, and elevating health care environmental standards across our high-rise community. Lindsay blends rigorous IDPH and OSHA compliance with forward-thinking operational strategies—ensuring our living spaces, clinical areas, and public environments are pristine, compliant, and continuously evolving.

Her background includes positions such as Director of Housekeeping and various manager roles for multiple Forbes 5 star resorts across the United States.

From Milwaukee, Wisconsin, Lindsay holds a bachelor's degree in Hospitality Business from The Broad College of Business at Michigan State University.

Director of Resident Experience

Director of Resident Experience

Nikki Gamble

Nikki started her career at The Clare in 2014 as the Life Enrichment Manager of The Terraces Healthcare. After over 11 years in that role, she joined the Director team in August of 2025.  As the Director of Resident Experience, her position is focused on planning a diverse range of events, outings, and community programming for Independent Living residents while overseeing the fitness department, community communications, and the front desk, concierge, and drivers.

An Iowa native, Nikki holds a Bachelor of Music Therapy from Wartburg College in Waverly, Iowa, and a Master’s Degree in Neurological Music Therapy from Colorado State University. She also completed the Therapeutic Recreation (CTRS) equivalency path at the University of Wisconsin-Milwaukee. She is a certified dementia practitioner (CDP) and is the Heartfelt Connections Champion for The Clare, providing dementia training to all newly hired staff. 

Nikki loves to incorporate creativity and music into her life in any way she can. She plays guitar, piano, and is a soprano in The Chicago Chamber Choir. She is also an avid outdoors person, enjoying fishing, camping, hiking, and has been a member of Scouting America, previously known as the Boy Scouts of America, for over 20 years. She is a proud pet parent of Jazmine, a Maine Coon mix, and Maya, a Pomsky (Pomeranian Husky), who is also therapy dog certified.

Director of Nursing

Director of Nursing

Kelli Gkigkinis, RN

Kelli joined The Clare’s Director Team as the Director of Nursing in June 2025, bringing a deep passion for patient care and years of hands-on clinical leadership experience. Born and raised in Chicago, Kelli began her academic journey as a history major at the University of Illinois in Champaign but discovered her true calling in nursing. She went on to earn her Bachelor of Science in Nursing from Chamberlain University and became a registered nurse.

Kelli began her nursing career at Northwestern Memorial Hospital as a medical-surgical nurse, then went on to provide specialized care as a ventilator nurse for developmentally disabled children and adults. Kelli first joined The Clare in 2022 as Assistant Director of Nursing, quickly proving herself to be a compassionate and dedicated leader. In addition to her current role, she has served as an Infection Preventionist since 2022 and was honored to speak at the 2024 National Association of County and City Health Officials (NACCHO) Summit in Chicago. She was also selected to join the LCS Clinical Leadership Council, a testament to her expertise and leadership in the field.

Outside of her professional life, Kelli has a lifelong love for music. She has played piano since the age of four, is currently learning guitar, and spent eight years as a singing waitress at Spavone’s Restaurante. A proud Cubs fan, she enjoys spending her free time walking along the lakefront with her chihuahua/terrier mix, Roxie.

Executive Chef
Hagop Hagopian, 3-star rated chef leading dining experiences at The Clare

Executive Chef

Hagop Hagopian

Executive Chef Hagop Hagopian has more than 20 years of culinary experience and many accomplishments. Notably, Hagop has received a 3-star rating from the Chicago Tribune and AAA Four Diamond status. He also participates in American Culinary Federation competitions and has performed kitchen stages in Michelin star-rated restaurants.

Hagop enjoys all aspects of culinary art including savory, gard manger, ice carving and pastry and confectionary arts. Hagop enjoys working with the residents, gathering their input and executing their ideas.

Chef Hagop enjoys spending time with his wife, daughter and two dogs when not at The Clare.

Director of Resident Health Services
Joanne Walsh Malleta, Director of Resident Health Services at The Clare in Chicago, IL

Director of Resident Health Services

Joanne Walsh Malleta

Social worker by trade, Joanne Walsh Malleta has worked in senior living for more than 30 years and joined The Clare in 2013. As Director of Resident Health Services, Joanne acts as a liaison between residents, staff and outside parties. She also meets with residents before they move to The Clare.

Joanne grew up on a farm in Iowa and graduated from the University of Iowa (the real U of I – she is a Hawkeye through and through!). She and her husband, Vijay have two children, Keaton and Nolan. Her family keeps her busy, but she also enjoys needlepoint, meditation, movies and concerts.

Director of Plant Operations

Director of Plant Operations

Dave Murphy

Dave Murphy joined The Clare as Director of Plant Operations, bringing more than 20 years of experience leading facilities, maintenance, life safety, and operational excellence across senior living, educational, and commercial environments. Throughout his career, he has built a reputation for developing strong teams, maintaining safe and welcoming communities, and ensuring residents and staff enjoy exceptional service and well-maintained facilities. Prior to joining The Clare, Dave held leadership positions in senior living, education, and commercial real estate, overseeing capital projects, preventive maintenance programs, regulatory compliance, and multi-site operations. 

Dave earned a Master of Industrial Technology and Operations from the Illinois Institute of Technology and holds numerous professional certifications in facilities management, safety, and building operations.
 
Outside of work, Dave enjoys spending time with his wife, Bridget, and their three daughters, Tara, Tess, and Mae. He is also kept busy by the family's beloved golden retriever-Labrador mix, Clancy. An active member of his community, Dave has coached youth sports for many years and enjoys helping others grow both personally and professionally.

Director of Human Resources
Michael Plowman, Director of Human Resources at The Clare senior living in Chicago

Director of Human Resources

Michael Plowman

As Director of Human Resources, Michael Plowman is responsible for implementing human resource management strategies to recruit, train and retain a high-performing and motivated workforce. He is responsible for developing and executing on-boarding, training and development, performance management, employee retention, benefits management and employee relations policies and strategies. The Clare has earned many awards over the years, including Choice Community Award for employee engagement and Holleran’s Highest Honors, which recognizes The Clare for exceeding expectations in employee engagement and satisfaction.

Before joining The Clare, Michael worked in the luxury sector of the hotel industry for more than 15 years, formerly with the Four Seasons Chicago and most recently at Waldorf Astoria Hotels and Resorts as the Director of Training and Development.

Outside of the office, you can find Michael hanging out with his miniature Schnauzer, Rocco and his miniature Wirehaired Dachshund, Frankie. He also enjoys trying new restaurants and traveling.

Medical Director at The Terraces at The Clare
Dr. Lee Lindquist, Medical Director of The Terraces at The Clare in Chicago, IL

Medical Director at The Terraces at The Clare

Dr. Lee Lindquist

Dr. Lee Lindquist has been the Medical Director of The Terraces at The Clare for over a decade. Her skill and experience are rooted deeply in geriatric care. She is the Chief of the Division of Geriatrics at Northwestern Medicine. Additionally. Dr. Lindquist is a Professor of Medicine at Northwestern University Feinberg School of Medicine, where she teaches and conducts innovative, patient-centered geriatric research. The Geriatric Division that Dr. Lindquist oversees is ranked #1 in Illinois and #8 in the country by U.S. News & World Report. Dr. Lindquist’s Northwestern alignment affords The Terraces at The Clare access to the medical center’s labs and EHRs, which deliver real-time information sharing with Northwestern physicians.

Dr. Lindquist’s geriatric expertise aside, she has a true passion for seniors and feels like they are a part of her family. Her highest priority in caring for seniors is to help keep them healthier longer and to remain as independent as possible.

Recognized nationally as a geriatric expert, Dr. Lindquist has been published in multiple medical journals and has been the geriatric voice for the New York Times, Harper’s, Boston Globe and Wall Street Journal. Appearing on CNN, MSNBC, and NPR, Dr. Lindquist has been tapped by multiple news sources to cover current geriatric patient care and medical issues.

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