3 Tips for Navigating and Negotiating the Dating Scene

Happy Valentine's Day! To celebrate this special day, Michelle Malawar, a bona fide love expert, outlines her negotiation tips for successful dating.

Negotiating is often thought of as a tactic -- a necessary life skill -- for the workplace and at home. AND, if you are single, there's no place like online dating where keen negotiation skills are not only important, but necessary to survive. But like negotiating in the workplace, there are many ways to make it easier and to do it gracefully.

I have helped dozens of men and women make romantic connections and after negotiating hundreds of online dates on behalf of my clients, I have learned a few key steps to making the process smoother.


When you've received a job offer, good negotiating advice is to wait for the organization or HR director to name your salary first.

This isn't true in the world of online dating. When it comes to scheduling a first date with someone you've met online, you're not being overly assertive by making the first move -- or by suggesting the specifics, if they've asked to meet. What you're doing is expediting the point of online dating: meeting in real life.

Suggest a place to meet with two or three times and dates you're available. Don't be wishy washy about what works for you. It will save you time, texting and hopefully, a headache.

Instead of an exchange looking like this:

Him: "You wanna grab a coffee sometime?"
You: "Sure. When?"
Him: "Tuesday after work?"
You: "I can't do Tuesday. Saturday?"
Him: "I'm doing a 60 mile bike ride with a buddy from college on Saturday. Sunday?"
You: "Yep, that works."
Him: "Where do you want to go?"
You: "I don't know....What're you thinking?"

...if you take the reigns, it can look like this:

Him: "...So what do you say we grab a coffee or drink sometime?"
You: "That would be great. I love the beer at Scion (and they have fried pickles, too!). Have you been? I'm free Tuesday and Thursday after work. But if you have another favorite place, I'm game, too. "
Him: "Whaaaaaaat...you can fry pickles?! That sounds amazing. Any chance you can do next Monday at 6:30 instead?"
Him: "Yes, that can work. Text me if anything comes up. My number is --- --- ----."

The point? Make an offer of where and when to meet. Give two or three times you're available. Name a place. If he has a strong preference for another place, he'll let you know. You're saving this man a lot thinking, and he'll thank you for it - trust me!


In negotiating, the term "BATNA" means "best alternative to a negotiated agreement." It means what your best option is if you don't get the deal you're going for. Basically, it's your Plan B.

When it comes to dating, the same is true: Know your BATNA. Aziz Ansari said it best about being single and dating: "It's like being a secretary in the shoddiest organization scheduling the dumbest shit with the flakiest people!" This is especially true of first dates scheduled online.

When you set a first date with someone you've met online, always have a Plan B in case he doesn't show up. If the date is at the coffee shop in your neighborhood and it's a five minute walk back to your house, great.

But what if you've traveled half an hour or an hour to meet him? In cases like that, I would choose an area you like walking around anyway (or for the practical-minded, near some errands you have to run). Rent the Runway and walking by the water is my BATNA in Georgetown. In Old Town Alexandria, it's reading a good book and having the pistachio gelato at Killer Espresso. Choose something you enjoy so you have a great day, whether you meet him or not.

3. Improvise As Needed

The ability to adapt and to hold your plans loosely is key in negotiating--and in dating, too. Michael Wheeler, professor of negotiation at the Harvard Business School, reveals how improvisation is essential to negotiating in his book The Art of Negotiation: How to Improvise Agreement in a Chaotic World. Adaptability is key, he says. It's about learning, exploring, adapting and influencing.

You might not get exactly what you want from a date. I only really, really like one in 20 men I meet online. That means for every one date I enjoy, there are 19 dates that are so-so. Maybe I'm picky and your number is less, but the likelihood is you're not going to meet "that special someone" right away. While you have these so-so dates, be open to the experience and what it brings.

In many cases, your romantic relationship begins with negotiating, even if only to set the details of where to meet. Negotiating is a practice that lasts throughout the relationship. The key to doing it gracefully, I've found, is to have a deep "YES!" inside that you're affirming. If you're not getting what you want or deserve, don't be discouraged. Onto the next.