7 Strategies for Successful Dating Later in Life

The wonderful thing about being older in today’s dating scene is that although it’s a whole different world now, many things remain the same – the anticipation, the butterflies, the thrill of maybe, just maybe, finding love. Whether you’re a newbie getting up to speed with all the sites and apps available or a dating rock star in the throes of the adventure, here are a few tips to Keep It Simple Sweetheart.

1. Figure out what matters

What are you looking for in a mate? Does it really matter if they like long walks on the beach? Too often, people date with no idea of what they really want and need in a partner, says psychologist, Cheryl Fraser, the author of the new book, Buddha’s Bedroom. Her suggestion? Before embarking on your quest, write a list of the top 10 attributes you’re after, highlighting a few deal-breakers if you have any. Next, ditch the concept of perfection all together. Go for seven out of 10, she says, and you’ll find a solid human being to have great fun and sex with and perhaps build a long-lasting relationship with, too.

2. Know what you’re after

How do you want to be loved? Ladies, is it enough that your man moves mountains to see you or must he scream his love from the mountaintop? According to Joel Sinclair, a relationship coach in Calgary, a common problem men have is they don’t know what purpose a relationship has in their life’s journey. If you want to write a book, say, the purpose of the relationship would be inspiration to help you reach that goal. Look for a dreamer or someone who admires people who shoot for the stars. The added benefit once you’re together is your partner will always know that only she brings this something special to your life, which helps to make her feel like the one.

3. Find your sweet spot…

Call me crazy or, worse, lazy but I have a spot near my home where I almost always arrange my first dates. No, I don’t want to have to commute across town just for what sometimes turns out to be a quickie (meet-and-greet, that is) but, more importantly, I like going to a place at which the wait staff know me, and I feel safe and secure. Other advantages? My sweet spot reflects my romance style so from the get-go, my guy knows I prefer a wine bar versus a coffee shop. And my approach avoids that insufferably polite back-and-forth thing strangers do when trying to pick a location. But what if a guy wants to stay close to home, too? Happily, most sites and apps have a proximity setting, which allows both parties to narrow the playing field of prospects and interact only with those close by. That said, gentlemen, if a lady insists on a spot near her, it might just mean that she finds safety in familiarity. She’s already meeting up with a complete stranger, so maybe her request for a first date on her home turf is not that big of an ask.

4. Dress with a system

Sometimes, especially if you’re new to a dating site, you’ll find yourself on a binge of first and second dates. Yay! The challenge when you’re going out with multiple people, however, is to remember what you wore the last time you went out with the one you’re seeing again, so you don’t end up wearing that, albeit adorable, LBD twice in a row. Me, I’ve developed a system. Although I change it up when I’m in the mood, I have a go-to first-date outfit and a go-to second-date outfit both carefully put together and adjusted to the season. This way, the only thing I have to keep track of is what number date I’m on. The downside? The folks at my sweet spot probably think I’m a one-dress wonder. But on the upside, I avoid the angst of rifling through the closet every time I’m about to go out the door, and I don’t have to go on a shopping spree to get me through a dating spree. A tip to men from one of my guy pals: even if you’re a T-shirt and jeans dude, step it up a notch, especially for the first outing. Don’t ever think ladies aren’t visual creatures, too.

5. Leave the past for later

Some boomers, with no long-term relationships in their history, worry they may be faced with questions as to why not. Other boomers, with multiple marriages in their history, worry about having to explain why. Most dating experts agree that prying questions about someone’s past have no place during initial encounters, so it’s okay to respond by saying you’d rather get into all of that once you get to know each other better. Julie Johnstone, a Hamilton-based relationship coach, points out, too, that there are different apps for different people seeking different types of encounters from just hook-ups to long-term dating. Make sure you’re using an app that attracts people who match who you are and what you’re after to minimize awkward moments and maximizes odds for success.

6. Sex is meaningful

When the aforementioned Dr. Fraser uttered this sentence, I immediately thought WTF? What about get-back-in-the-sack initiations, just-roll-with-it romps or friends-with-benefits booty calls? They still mean something, she insists. Fair enough. Each person has his or her personal sexual compass, and even if yours is always pointing north, to keep life simple, own it. Of course, if you’re coming off a long-term monogamous relationship or if you haven’t got naked in a long while, you might have to experiment a bit to discover what sex means to you now. After each encounter, take some alone time to process and identify your feelings.

7. When to hold ’em…

Know when to walk away (you’re bored) and know when to run (alarm bells!). Sure, you’re not looking for perfection but dating someone more than a few times just so you’re not alone is not cool, not smart, and it can be exhausting. In fact, it contributes to burnout. Here’s the thing: although being footloose and fancy-free is often exhilarating and empowering, from time to time, the whole process of courting can bring on dating fatigue, which is why, I think, a lot of people on dating sites say they can’t wait to get off them. So do. Make a final swipe left. Dating isn’t supposed to be about hanging in there at all costs so if you’re not feeling the love, take a break. After all, you’re not married to it.