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How to Get a Second Date With a Great Guy

By: Tara Bradford

When you are a single, successful woman it can be easy to get frustrated with the dating scene. Not only do you feel like you have gone on a million first dates and you might as well be on The Bachelorette, but your family has also threatened to nominate you for the show.

GIF via Giphy.com

GIF via Giphy.com

You hope they are joking about The Bachelorette, but in the back of your mind you wonder if that is your only hope at finding a great guy. Let’s be honest, the success rate of that show isn’t very encouraging either. Beyond those jokes, you also have your grandmother asking you when you’re going to settle down and saying things like, “You will meet a nice guy one day”. You might even get in your own head as you are scrolling through social media seeing all of the engagements and weddings, and you find yourself judging yourself for still being single.

The thing is, you really want to meet a great guy but you have no idea where they are all hiding. You have been on dates and they don’t go anywhere. You’ve read books about manifesting your dream guy and so you have made a list of everything you are looking for. Your list might look something like this:

  • Professional
  • Intelligent
  • Articulate
  • Affectionate
  • Successful (with a particular income bracket in mind)
  • Serious about a relationship
  • Wants kids/Doesn’t want kids

When I started writing this article, I wondered how I was going to find out where all of the great guys were hiding. Initially, I thought I could send out a survey to a variety of single men and try to look for patterns in what they were looking for. What I found was that each and every one of them wanted something different. I then pulled my own skeletons out of the closet and revisited “the ghosts of dating past” and thought that most of the men who I pre-screened for dates had told me they were looking for “a nice girl”. That seemed too basic.

After getting nowhere with all of that I decided I better call in an expert. Dr. Siva Sundar weighed in on “the list” and his response was, “You have to realize that men don’t come pre-packaged like that.”

Image provided by author

Image provided by author

Dr. Siva is a practicing physician and a coach who helps professional women find relationships with quality men. He started his coaching practice because he had issues in his own romantic life and he wanted to figure out what was going on, but also because he kept hearing women say that there was a shortage of educated men. As a successful man, he felt that was really interesting and began giving advice to both men and women. He agrees that both men and women have their lists and that while women have a relatively long list of things they are looking for and men have a much shorter list, we are all really looking for the same thing: connection.

“The problem is that we are taking very different routes to get there and we both have a lot of assumptions hidden beneath those lists we have made.”

Dr. Siva did offer some advice on how we can allow a connection to happen naturally by suggesting one thing you can change today to increase your second date success rate: change the focus of the conversation. Successful, driven women tend to lead with their careers. It is usually the thing that we feel most comfortable talking about and most confident with. “The problem with talking about work or your career the entire night is that you walk away and you don’t feel much of a connection or chemistry.”

Why does this happen?

Dr. Siva returns to “the list” as an example. “Ladies, think about your list. In the grand scheme of things if someone came up to you and said, “I found the perfect guy for you! He is super attractive and has a six pack.” How would you rank having a six pack on your list of 10 things you are looking for? It’s likely close to the bottom.”

Now, look at it from a man’s perspective. “Telling a man who is already successful how successful you are is kind of like your friend telling you the perfect man for you has a six-pack. They think that’s attractive, but they also want to know if you are nice, kind, and supportive.”

Men are results focused.

The great guys (who fulfill some of the things on your list) want to have more fun. Dr. Siva reminds us that “their first encounters with women is with their mothers so they think of women as kind, caring, supportive, loyal and fun. And that is what they are looking for deep down.”

As a successful and driven woman, you could also think of it in the sense of running a business: you wouldn’t hire an employee who is really good at all of the same things you are good at, would you? Men look at dating in the same way, which is why they want to know that your qualities complement their own rather than competing with them. Naturally, both men and women want what they do not have enough of. If you both have been successful in your careers then it is a great opportunity to look for connection beyond your professional accomplishments.

Image provided by author

Image provided by author

Dr. Siva believes the thing that sets women apart, and helps them find more of the men they are looking to meet, is when they learn to not only be successful but also accomplished.

“Quality and successful men tend to go for women who are accomplished, not successful. Accomplished women are really good at something that those men are not already good at. To clarify, we do go for success, but it’s a secondary priority below being accomplished, attractive, nice, fun, loyal, and supportive.”

This brings us back to “the list”. Again men have a very different list than women and we see that success pops up on both of them at different positions. It can be misleading to think we are all looking for the same thing because even though we use the same words to describe what we are looking for we often assign a different meaning to them. For men success usually means multiple six-figure salaries, private jets, yachts, and fancy cars; while women define success as feeling independent and not needing to rely on anyone. There are those assumptions again...

While you can’t predict what every great guy is looking for, if you can lead with something other than your career on a first date, then you are more likely to get a second date. You will also score bonus points if he perceives you as nice, kind, and fun because when he doesn’t feel like he is competing with your success then it invites him to be more fun and playful too. This is what creates chemistry and, hopefully, a lasting connection -- the thing we can both agree on when we throw those lists (and assumptions) out the window.

Want to get personalized feedback from Dr. Siva? Click here to take his quiz and find out how you can fine-tune your approach to dating based on the type of woman you are in his free webinar.


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Tara Rae Bradford is a certified life coach. She is the founder of The Potentialista®, an international coaching program to help you work through a major life transition such as a break-up or divorce so that you can go from surviving to thriving. Tara has 8 years of experience helping individuals and families through tragedies as a critical care nurse and 2 years of experience in healthcare administration and hospital operations. After reinventing her own life, she completed her certification in coaching so she could help others see what they are exceptionally good at so they can use that to enrich their own lives and the lives of others.

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