Dating Advice
Top 5 Tips for Dating Over 40
Dating over 40 is not a setback — it's an opportunity. Learn how to approach dating with wisdom, self-awareness, and confidence to build meaningful relationships.
Lisa Galos
6 min read
Dating Advice & Relationship Tips
Expert insights and practical guidance to help you navigate modern dating, build meaningful connections, and create lasting relationships.
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Dating Advice
The History of Matchmaking
From ancient traditions to modern love, matchmaking has been a cornerstone of human connection for centuries. Discover how this timeless practice has evolved.
Lisa Galos
7 min read
Dating Advice
Balancing a Busy Professional Schedule with Dating
You don't have to choose between success and love. Learn how to balance a thriving career with a fulfilling dating life through intentional planning and effective communication.
Lisa Galos
5 min read
Dating Advice
Are Dating Services Worth It?
Dating services come in various forms, from traditional matchmaking to modern online platforms. Each offers unique features and benefits, but the goal remains the same: to help you find a meaningful connection.
Lisa Galos
8 min read
Dating Advice
Do Dating Services Work?
An in-depth look at the effectiveness of high-end matchmaking. Learn why professional dating services work and how they compare to mainstream dating apps.
Lisa Galos
10 min read
Dating Advice
Matchmaking vs. Dating Apps in 2025: Why High-Touch Services Are Surging
Disillusioned with algorithmic swipes, singles—especially discerning professionals—are moving to high-touch, human-led matchmaking. Below we compare approach, outcomes, time cost, privacy, and total investment so you can decide which path fits your goals.
Lisa Galos
7 min read
Dating Advice
How Much Does a Professional Matchmaker Cost in 2025?
If you're vetting services for a serious, long-term relationship, you'll find a wide price spectrum. Below we break down tiers, what's included, and how to evaluate ROI vs. app spending.
Lisa Galos
5 min read
Dating Advice
12 Things to Look for in a Matchmaking Company (and 6 Red Flags)
Not all matchmakers are the same. Use this practical checklist to compare services and avoid costly missteps.
Lisa Galos
6 min read
Dating Advice
Is a Matchmaker Worth It?
An honest look at whether a matchmaker is worth the money — what you're really paying for, who it fits, who should skip it, and how to weigh the cost.
Anna Rigali
7 min read
Dating Advice
What Does a Matchmaker Do?
What does a matchmaker actually do? A clear look at the real process — intake, vetting, curated introductions, and feedback — and how it differs from apps.
Anna Rigali
6 min read
Dating Advice
Matchmaker vs It's Just Lunch
Comparing a local Chicago matchmaker with It's Just Lunch — how the two models differ on personal attention, vetting, local knowledge, and discretion.
Anna Rigali
6 min read
Dating Advice
Jewish Matchmaking in Chicago
A Jewish matchmaker, or shadchan, makes discreet, values-aligned introductions for Chicago singles and families who want a partner who shares their faith.
Lisa Galos
7 min read
Dating Advice
Dating Over 50 in Chicago
A practical, honest guide to dating over 50 in Chicago — why now is a great time to meet someone, how to skip the app fatigue, and how a matchmaker can help.
Anna Rigali
7 min read
Dating Advice
Finding Love After 60
Finding love after 60 is more possible than you think — a gentle, practical guide to dating in a new chapter, with companionship, confidence, and real help.
Lisa Galos
8 min read
Dating Advice
Dating After Divorce in Chicago
A warm, honest guide to dating after divorce in Chicago — when you're ready, what's changed, and how a matchmaker helps you meet someone worth your time.
Anna Rigali
7 min read
Dating Advice
Burned Out on Dating Apps?
Dating app burnout is real, and you're not imagining it. Here's what the research shows, why the apps feel like work, and a calmer way to meet someone in Chicago.
Anna Rigali
6 min read
Dating Advice
Best Date Spots in Chicago
Where to take a date in Chicago and the suburbs — relaxed first-date spots and romantic date nights, from West Loop wine bars to the Naperville Riverwalk.
Anna Rigali
7 min read
Dating Advice
A Matchmaker's Success Rate
Wondering about a matchmaker's success rate? An honest, sourced look at what success really means and why there's no single industry number to trust.
Anna Rigali
6 min read
Dating Advice
How Matchmakers Vet Clients
Worried about who you'll actually meet? Here's exactly how a professional matchmaker vets and screens clients, from identity checks to real conversations.
Anna Rigali
7 min read
Dating Advice
Elite vs. Selective Search
Comparing Selective Search with a local Chicago matchmaker? An honest, fair look at national scale versus a hands-on mother-daughter team.
Anna Rigali
6 min read