10/02/2013 03:23 pm ET Updated Jan 23, 2014

He Said, She Said: How to Date Better

What makes a good first date? I'm not talking about where to go or what to do. I'm talking about what kind of a person makes a good first impression on a date. For this installment of he said/she said, I turned to Taylor Jacobson, leadership and life coach, for his thoughts and perspective about what it takes to wow someone new.

Neely: What do you think are some qualities in a woman that make for a great first date?

TJ: By far the most important quality is being willing to share something real and go into the details without being prompted a million times.

When people talk about being a great conversationalist, they talk about asking questions. And that's critical. But the questions only take a conversation so far. If you're not willing to take my question and give me some substance in return, the well is going to run dry pretty quickly.

Remember, it's not only easier to go deep on a topic, it's also a better way of building rapport and establishing if there's any real connection. In contrast, when you give short answers and aren't willing to open up, it forces me to change topics and creates a mutual experience of skimming across the surface. You get a first date that is superficial and hard work. Not good.

I would encourage women to talk about your experience and what's real for you. Don't be bashful about it. Be interested in your own life and confident that you're worth talking about and you make it much easier for a guy to engage you.

Neely: I couldn't agree more! This is why I always say there is no such thing as a bad date. OK, maybe there is (I've heard some doozies), but the point is, people who say they're not great conversationalists or bad at small talk NEED dates to practice becoming a better dater, someone with whom others can more easily connect. You can't just expect that something that doesn't come naturally to you will all of a sudden just happen.

You can look at dates as opportunities to practice various dating and interpersonal skills. So, it can actually work out quite well if you have dates where there's no romantic spark, because the pressure is off a bit. You can use those situations to learn about someone new and work on things about yourself that you've already identified you need to work on. This way, you're preparing yourself to attract the guys you really do like rather than repel them. I encourage women to see all of their dating experiences as purposeful.

That's what entrepreneurial dating is all about!

TJ: This is great advice. If you want a way to practice your networking and conversation skills, there is no better way than going on a bunch of low-stakes dates.

Ironically, the more we really want to perform, the more likely we are to show up as strained and stressed out, which is unattractive because your date will feel your stress and subconsciously get stressed out too.

Guys make the mistake of thinking that they have to do or say something "right" -- funny, smart, impressive -- but the truth is that what matters is how you make the other person feel.

More than anything, you are an outstanding date (and human being really) by making people feel good around you. I think that happens when you are genuinely relaxed, confident and transparent -- we talked earlier about being willing to go deep on topics -- because you create an atmosphere where it's safe to come as you are.

Do you find that to be true? What do you advise women to do to relax and generate real confidence?

Neely: Yeah, and when you are in that zone of confidence and authenticity, you also create a place where it's safe for your date to come as he or she is -- so it's a win-win.

Confidence comes with time and practice. It's really a learned skill (I work on it every day!), and it doesn't just happen through affirmations; it takes action and experimentation. If a woman is anxious on dates because she's scared of being rejected, I'd tell her to get out there and start talking more to men at bars or parties -- put herself on the line. She'll start to see that rejection isn't so terrible, and when she goes into her dates without that fear of rejection, without an attachment to the outcome, she'll find that she can relax more and be more authentic.

When you look at dating as more than an interview for marriage and babies, but as an opportunity for discovery, self-growth and personal development, you're not solely focused on the outcome, so you can direct your energies more positively and productively (e.g., being more in the present moment, offering more authenticity, asking more questions, articulating your passions, etc.). Over time and with practice, you develop an ability to sit back and relax and be confident in your own skin -- those qualities start to come more naturally.

I think also a piece of this is recognizing those people who you really feel you can be yourself around, instead of trying so hard with those people who you feel you need to twist yourself into a pretzel for. Been there, done that.

What about you? How would you advise a woman to find that place of authenticity and relaxation on first dates?

TJ: For men and women, the best way to learn real confidence is to practice transparency. Real confidence means that you're comfortable with all of you and don't have anything to hide.

If you're not comfortable with all the parts of you, you wind up trying to present a certain package, and that takes effort. Again, that shows up as strained in your body language and tone of voice. Real confidence is effortless because you're not worried if you'll "get it right."

At first, practicing transparency feels difficult and risky. We've got parts of ourselves that we judge and want to keep under wraps. But over time, you start to experience how liberating it is to be transparent and you learn a kind of unconditional confidence that is very relaxed, open and authentic. That sets anyone at ease, including your date, guy or girl.

One word of caution: When we're completely authentic, yes we're open and honest, but that doesn't mean that you tell a guy he's poorly dressed or stare at a woman's breasts because that's what you're thinking about. When we say "honesty," what we do NOT mean is having no filter.

The best filter by far is to ask ourselves if what we're saying and doing is in service of the other person. In other words, "How can I say this in a way that leaves the other person feeling good?" That is attraction in a nutshell.

Neely: Amen!

Taylor Jacobson is based online at, where he helps people do big, fulfilling things. For practical ideas on how to transform your career, health and relationships, join his free newsletter.