The Best Strategies for Dating Success

November 17, 2017

This is Part III of a series on giving yourself a Dating Makeover. Part I: Give Yourself a Dating Makeover may be found HERE. Part II: Designing Your New Approach to Dating may be found HERE.

dating coupleIn my last two posts I’ve provided a framework for thinking about how to be more successful at dating by changing your strategies (and mental state). Today I’ll provide lots of specific ideas for kick-starting your new dating life. Keep in mind, though, that my suggestions are far from comprehensive. The sky’s the limit here – your strategies are limited only by your imagination.

Getting Out of Your Comfort Zone

The most important element of any change is the willingness to try new things. The same old strategies will result in the same outcomes – which is fine if you’re killing it. But if you feel like you aren’t getting the results you want, you need to implement some new plans. New ventures always include some risk, but they’re also the only way to realize new benefits.

I encourage clients to do one new thing per week. I know it’s doable because I do it myself. My own goal is more about general self-development rather than dating, but the principle is the same. So far this month I’ve enrolled in a watercolor painting class and dropped in at a meditation workshop. I’ve met new people and gotten excited about new activities.

When trying to meet new people to date, it makes sense to focus on activities that feature your “target market.” You’re better off volunteering for a Habitat for Humanity build than signing up to be a Big Sister, because you’re more likely to meet guys you can potentially date there. Here are more suggestions:

Online Dating

It accounts for up to a third of American marriages, so ignore it at your peril. Online dating can be frustrating as you look for the right platform. It’s time consuming and responding to messages can quickly become an overwhelming chore. It’s also hard to filter for people who are in it for a serious relationship. Still, it’s got a huge customer base, which means many potential matching opportunities. If you’re avoiding online dating, resolve to try out one new platform this week.


Twenty percent of married couples meet through work. While dating someone in the office can be tricky, there are ways to meet people in your company and industry through networking. Go to events sponsored by your company, alumni association, and industry trade group or governing board. Networking can feel awkward, even for those of us who are extroverts. The only way to do it is to take the plunge – approach a stranger and introduce yourself, or ask for an introduction from a friend or colleague.


Go to your local museum’s events. In Boston, the Museum of Fine Arts sponsors tons of events, including some for singles. Take a cooking class for singles. Attend a lecture at a local university. Go hear an author read from their new book at your local bookstore.

I’ve done all of these things, and sometimes I haven’t exchanged a single word with another person. Other times I’ve had great conversations. It’ll be hit or miss, but remember that you miss 100% of the shots you never take.

An important benefit of learning is that it makes you a more interesting person. There is no better investment of your time than this.


One-off commitments like serving a holiday dinner at the shelter are great, but becoming a regular for a cause you care about is even better. Young people place great importance on dating people who share their values – what better way of filtering for that?

I recently read a story by a woman who had gone on a date and felt “no spark.” She reluctantly agreed to a second date. Conversation flowed more easily and they went for a walk after they left the restaurant. Suddenly a homeless man said “Hi Joe!” She was taken aback and asked her date how he knew this man. It turned out he was a regular at one of the shelters and very popular with the guests. She’s been married to Joe for years now, but she credits that moment for creating the “spark.”

Join a Team

Last month I went to a wedding between two people who met on a coed soccer team in Boston. They both played in college and joined when they moved here so they could meet some new people. Again, this was a great filter – by pursuing their own interest, they met a partner who shared it.

Another good option is to join a meetup group if they’re active in your area. I know a woman who is an avid hiker and met her husband through the Appalachian Mountain Club.

Eat at the Bar

Eating out alone is kinda scary. At least I’ve always found it so. Last week I travelled to Montana for a wedding. I was alone and there was no way I was going to sit in my hotel room in such a beautiful place. I went out to eat several times on my own. I even had to put my name in at a cafe as a party of one, which felt sort of lame. But it was OK. I read my Kindle and had a great breakfast. The best experience I had was sitting at a sushi bar and chatting with the people next to me.

I have one friend who is single and forces herself to regularly go out and eat at the bar on a weeknight. She has met a lot of men this way! It’s funny, she even has formed opinions about what kinds of guys she meets in different neighborhoods. Several good conversations have led to dinner dates.

The key: Introduce yourself. Flirt when appropriate.

Create a Dating Support Network

The most common way spouses meet is through friends. Your social circle has a lot of potential, but most people don’t make the most of it. It’s important to nurture existing relationships – for many reasons – but specifically to make the most of connections to possible dating partners.

  • Be open with friends, family and coworkers when appropriate. Don’t be shy – let people know in a matter of fact way that you are seeking a relationship and would like to meet some new people. There’s nothing shameful in this – in fact, people will respect your efforts to realize your goal by speaking up. Be OK with setups, blind dates, etc.
  • If there’s someone you’d like to meet, ask for an introduction. You don’t have to indicate a desire to date the person, you can express a desire to meet them because they seem interesting or appealing in a general way.
  • Accept as many invitations as you can. We all know the feeling of preferring to stay in when we’re tired, the weather’s bad, or the event doesn’t sound like all that much fun. Don’t give in to that impulse. Force yourself to make an effort – the more sociable you are, the more people will keep you in mind for future social opportunities.
  • Host gatherings of your own. One of my favorite ideas came from a guy who hosted a brunch for about ten friends. He asked each one to bring someone the rest of the group didn’t know. It was a big success, because everyone there knew someone but also got to meet a bunch of new people. Friendsgiving would be another great idea – think “the more the merrier.”

Adopt New Productive Habits and Behaviors

Negotiating Dating and Relationships

Resolve to do the following:

Be honest from the start about what you are looking for in life. Whether it’s a boyfriend or marriage and children, the only people you’ll scare away with honest disclosure are those who don’t share your goals. This is one of the most important filters in dating and can save you a lot of heartache.

Stop curating your life on social media. I was just reading a book review in The Guardian and came across this great quote:

“Profound loneliness is by many accounts one of the great scourges of our age, when everyone is meant to be having the most amazing time eating avocados with their friends on Instagram.”

Facebook did a study where they looked at accounts where the relationship status had gone from “in a relationship” or “engaged” to “single.” They found that photos of the couple looking blissfully happy were posted right up to the day of the breakup. You can’t control what others post but you can stop contributing to the madness. You can also remind yourself that things are not perfect for anyone no matter what their pics show.

Be realistic in your expectations.

Don’t expect a commitment after two dates – if it’s offered you probably can’t trust it. On the other hand, don’t expect a guy who “doesn’t know what he wants” to suddenly wake up and realize he’s in love with you. Successful relationships are characterized by beginnings that are free of drama and worry.

Set boundaries and demand respect by enforcing them. Whether it’s “I don’t make plans after 10 p.m.,”  “I don’t do casual” or “I don’t have unprotected sex,” decide where your limits are and be consistent.

Heed red flags.

The most heartbreaking part of blogging is hearing the stories of women who have ignored red flags to the point where they’ve wasted precious months or even years. They’ve tied themselves in emotional knots. They write to ask how they can fix their relationships as they describe terrible, cruel behavior from their boyfriends. All I can do is encourage them to fix themselves with the help of a counselor.

If you don’t feel right about something in your gut, if your friends think you are being treated poorly, if you’ve caught your partner lying, PAY ATTENTION. It’s the relationship equivalent of a car alarm that won’t shut up.

Care for Yourself


If you are good at caring for yourself, you signal that you have the capacity for care for others. Depressed people are self-absorbed by definition. When you have your act together, you radiate high quality.

  • Get enough sleep.
  • Move.
  • Eat healthy food.
  • Don’t drink too much or use harmful substances.

Pay special attention to grooming.

  • Dress to flatter your body in clothes that make you feel confident. If you don’t have a good sense for this, consider Stitch Fix or find a small store where the owner can help you pick stuff out.
  • Find a good hair stylist. A great haircut will make a difference. You may want color or highlights. Be prepared to pay – your hair is something you wear 24/7.
  • Take good care of your skin and wear makeup. Sephora is your friend. Read the reviews online and then go in and ask them to do your makeup.


Manage stress. Whether through exercise, meditation or some other activity that relaxes you, it’s important to be able to relax on a date. Anxiety makes everyone less attractive.

Risk vulnerability. You can’t fall in love or be loved if you don’t open your heart. If that feels impossible, intimacy will be impossible. Do the work you need to before dating seriously. It will be time well spent.

I guarantee that if you implement the main strategies I’ve outlined here, your dating life will improve. Like any goal, it requires planning and follow through to be successful. But you can’t say you don’t know where to begin. This is the roadmap.