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Dating Advice from the Professional Matchmakers

Dating in Boston

Our professional dating experts provide you with tips on how to date in Boston, from great first date locations, to where to go to find single men and women.

Boston Dating Isn’t Broken — Expectations Are

Boston Isn’t the Problem Most People Think It Is At LunchDates, we spend a lot of time talking with single professionals throughout Boston. The conversations…
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Where to Meet Singles in Boston This Fall (Without Relying on Apps)

In a city filled with professionals, academics, and creatives, Boston offers countless ways to meet singles naturally. While dating apps focus on profiles, real life…
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Why Boston Singles Don’t Have Time for Apps — And What They’re Doing Instead

Dating apps promised endless options, but for many Boston professionals, that promise has turned into exhaustion. A recent Forbes Health survey found that nearly 78%…
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Benefits of Professional Matchmaking

More and more people are turning towards the personal touch of a professional matchmaker to find that special someone. Find out why a matchmaker might be right for you.

Do Matchmakers Work? Why Some People Get Results from Matchmaking

One of the most common questions people ask before hiring a matchmaker is simple: Do matchmakers actually work? The honest answer is yes, matchmaking can…
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What Happens When You Hire a Matchmaker? A Step-by-Step Look

Most people have a general idea of what matchmaking is. They assume it means being introduced to people who have been screened in some way….
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What Matchmakers Notice in the First 30 Days That Singles Miss

The first month of dating someone new can be exciting, confusing, and full of possibility. It can also be hard to read clearly. When you…
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Age Specific Advice

Sure, age might just be a number, but each decade brings along with it a set of unique dating challenges. Our professional dating experts provide advice on how to overcome the specific trials men and women face in their 20’s, 30’s, 40’s, 50’s and beyond.

Dating After 60: Embracing New Opportunities for Love

Dating in your 60s isn’t about starting over—it’s about starting fresh. Whether you’re newly single or simply ready to reconnect with this part of your…
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Dating Over 50 in Boston: Unique Challenges and How Matchmaking Helps

Dating in your 50s can be both exciting and daunting, especially in a bustling, achievement-focused city like Boston. For singles over 50, dating often shifts…
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Finding Love After 50: How to Start Dating Again With Confidence

Dating after 50 can feel like entering a new world—but it’s also one of the best times to find a meaningful connection. By age 50,…
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Dating Advice

Dating isn’t easy. Our team of dating experts answer a wide range of common dating questions to provide you with a solid foundation for finding love in an ever-changing dating landscape.

Why Smart, Successful People Overthink Dating

Highly intelligent, successful people tend to approach problems the same way: gather information, analyze options, reduce risk, and make the most rational decision possible. That…
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How to Tell If You’re Dating With Intention — Or Just Staying Busy

Many singles assume they’re dating intentionally because they’re dating often. The calendar looks full. Messages are active. Dates are happening. But frequency doesn’t equal direction….
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Emotional Availability: What It Actually Looks Like (And Why It’s Rare)

Emotional availability is one of the most talked-about — and misunderstood — concepts in modern dating. People often use it as shorthand for chemistry or…
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Dating Coach Advice

Have you ever thought your dating game needed a little help? Could you use some advice from somebody who has the training and experience to be a professional dating coach? Find out more about how a dating coach can improve your dating success.

Boston Matchmaker vs. Dating Coach: Which One Do You Need?

We often hear this question: “Do I need a dating coach or a matchmaker?” The answer depends on where you are in your dating journey…
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What Is a Dating Coach? And Do You Need One?

You’ve probably heard of dating coaches, but what exactly do they do—and could one help you? Think of a dating coach like a personal trainer…
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Why I Decided to Work with a Dating Coach (And What Changed)

Hiring a dating coach wasn’t something I ever thought I’d do. I used to believe dating success came down to luck or chemistry—but after years…
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First Date Advice

Is there anything more nerve wracking then a first date? It doesn’t have to be that way when you go in knowing the do’s and don’ts of a first date. Our dating gurus dish out all the intimate details on what it takes to make a first date successful.

8 First-Date Tips for Boston Professionals

First dates can be exciting—and a bit nerve-wracking—especially if it’s been a while or you’re used to serious commitments. In a city like Boston, where…
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What Makes a Great First Date? Tips for Creating Lasting Impressions

For professionals in Boston, time is limited, and expectations are high—especially when it comes to dating. First dates matter. They either open the door to…
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What to Talk About on a First Date in Boston

First dates are a great chance to connect—but if you’re feeling nervous, you’re not alone. A good conversation can reveal much about someone’s personality, while…
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Online Dating

Online dating is quick, easy but often leaves you wanting more. Sliding left or right is no match for finding that right person through a professional matchmaker. If you are going to use an online dating app, LunchDates has some advice on how to avoid the pitfalls and hazards singles often fall for when searching for love online.

What Does a Verified Dating Profile Really Mean? A Guide for Boston Professionals

A verified dating profile usually means that the person completed a specific check required or offered by the app. Depending on the platform, that check…
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Matchmaking vs Dating Apps for Professionals in Boston (2026 Guide)

Dating apps and professional matchmaking can both lead to introductions. The real difference is how much of the process you want to manage yourself—and how…
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Does Tinder Work in Boston? What Professionals Should Know

Tinder can work in Boston. It gives singles access to a large pool of people, makes it easy to start conversations, and has a low…
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Seasonal Advice

Does Valentine’s Day give you the dating blues? How can you survive being single over the holidays? Need some great outdoor dating ideas during the warm summer months? As the seasons change, so do dating strategies. Our experts provide you with top seasonal advice for year round dating success.

Valentine’s Day Isn’t the Hard Part — It’s What Comes After

Valentine’s Day tends to get all the attention, but for singles, the more revealing moment often comes a week or two later. Once the dinners,…
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What Matchmakers Wish Singles Knew Before the Holidays

There’s a lot of advice floating around this time of year — some good, some not so good, and some that just makes singles feel…
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How Boston Singles Can Make Finding Love Their 2026 Resolution

Every December, I hear the same thing from singles across Boston: “Next year, I’m actually going to prioritize dating.” The intention is solid — but…
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