7 Tips for Dating the Second Time Around (Ahead of Golden Bachelorette)

Hello September! 

Summer’s almost gone, and there’s a trifecta happening in the dating world. It’s an exciting time for singles who desire to change their relationship status leading into the Fall and the holiday season.

Here’s why there’s a dating trifecta going on, right now.

1. Summer romances are fading.

2. More singles are looking for love leading into “Cuffing Season” and the holidays.

3. And the drumroll please—the Golden Bachelorette season premiere is around the corner on ABC on September 18, 2024.

Just in time for these dating trends, I’m excited to share that my dating advice is featured in the September Issue of Northern Virginia magazine. In the article “Second Time Around,” Seniors and dating experts share tips on finding love in your golden years,” I shared seven tips for singles over 50.

Related: The Cyber-Dating Expert Guide to Cuffing Season

Let’s Get Started

TIP 1: Let the world know you’re ready to date.

Start by asking your friends and family if they know someone special to introduce you to. Look within your local community to meet new people. Consider taking a class at a senior center or a community college, joining a book club, or volunteering at a non-profile or a museum.

TIP 2: You need both an online and offline strategy.

Getting back into the dating game at any age is challenging, but it’s easier now to find someone 50+ with the massive popularity of online dating. Plus, did you know twice as many couples meet online than through friends? It’s time to create an irresistible dating profile to attract your perfect match.

TIP 3: Write down your dating intentions.

It’s essential to know the type of relationship you’re looking for.

Being specific about your dating intentions and knowing your end goal before you start your search, will help you find compatible matches. Realize that some singles want to go on an abundance of dates to meet new people, while others know they’re looking for a committed relationship with one partner. 

It’s easy to determine, by noting your potential date’s relationship goals in their profile. Or take the to discuss the type of relationship you desire with your date when you think you’ve made a connection to make sure you’re on the same page.

Related: The Upward Trend of Older Women Dating Younger Men

TIP 4: Discuss your dating plan with family.

By now, you and those you hope to attract might have an extended family, including children and grandchildren. Before you start dating again, discuss your desire to partner with your family for them to get on board with your plan.

Once you meet someone especial, ask them about the importance of time they spend with their family before you start blending. Does one person spend every Sunday with their grandchildren? Are they from a split family and only get to see them every other weekend, or do they live out of town?

Understand that bringing someone new into your family mix can wait until you mutually decide to become exclusive to avoid confusion and revolving doors with family members.

Once you’ve got a steady date, it’s time to have conversations to ensure you’re on the same page, which brings us to Tip #5.

TIP5: Confirm your relationship type with your partner. 

When looking for love a second or third time around, you’ve learned a lot of lessons from your past. Knowing that you’re embarking on a new (and possibly last) chapter with a partner, it’s time to ask some key questions for compatibility.

From deciding on relationship labels (boyfriend/girlfriend, partner, significant other) to monogamy or non-monogamy, marriage or life partner, you shouldn’t play a guessing game or walk on eggshells in your new relationship. 

TIP 6: Let’s talk about money. 

Being fiscally responsible and having a good credit score is the new sexy. But when should you have the money talk? While it might not sound romantic, it’s responsible, and essential.

Some questions to discuss with your partner include, Will you be combining finances or keeping them separate? Who will pay for vacations, entertainment, and dates? Is one person a saver, while the other is a spender? Money and finances can make or break a relationship so I recommend asking these questions to ensure a healthy romantic journey.

TIP 7: To relocate, or not to relocate.

Long-distance dating has become more popular, in part, due to the growth of online dating. I always says, “Don’t Get Hung up on Zip Codes,” when you start dating again. Many singles will move for love, and often with thanks to technology, people can work remotely. 

Ask your partner if their goal is to live under the same roof or if they prefer to maintain two separate households. 

As you recall, in the Golden Bachelor, Theresa Nist and Gerry Turner could not agree on where to live, and this issue was a critical factor in the demise of their short-lived marriage.

However, with several hundred million singles dating online worldwide, zip codes and distance are not barriers to finding love.

Finally, Don’t give up.

If you forge a relationship that runs its course after six to 12 weeks, don’t panic. Love doesn’t have an expiration date, and everyone deserves a second or third chance to find someone special. 

Wishing you much love and joy in cyberspace, or wherever you may swipe or roam.

Julie Spira is America’s Top Online Dating Expert. She’s an award-winning dating coach who’s been helping singles find love online for 25+ years. Follow @JulieSpira on IG.