How To Feel Less Vulnerable When Asking For What You Want


The year was 2012.

My first ever serious boyfriend texted me midday “Happy Valentine’s Day. Why don’t I come over after work?” I felt vulnerable from his display of care and attention and replied, “You don’t have to do that.” He said, “It’s Valentine’s Day, yes I do.”

He showed up at my house with a bouquet of flowers in hand and I welcomed him inside. I was feeling a bit awkward, though—I’d never had a serious boyfriend on Valentine’s Day before. This was new territory.

We were sitting in my living room while one of my roommates watched TV when he shyly asked, “So, what do you want to do tonight?”

I answered, “I don’t know, what do you want to do?”

My roommate witnessed this painfully uncomfortable exchange and chimed in, “You guys, you actually have someone to spend Valentine’s Day with—go out and do something!”

The truth is, I knew exactly what I wanted to be doing on Valentine’s Day night. I wanted him to have already made us a dinner reservation at a fancy restaurant downtown or by the beach. I pictured us going for a walk along the water or amongst the city lights and skyscrapers after dinner, romantically holding hands, kissing, talking about the meaning of life. Maybe we’d walk past a street performer and slow dance to some Jazz music, laugh, and fall in love.

You know, like the normal Valentine’s Day fantasy.

The reality is, we spent Valentine’s Day at a Baskin Robbins in a strip mall, silently eating ice cream in February because I didn’t have the skills to hold the weight of my desire and I didn’t know how to clearly communicate how I wanted to spend the night with him. He felt self-conscious because he was doing what he thought was right, having asked me how I wanted to spend the evening assuming I’d honestly tell him what I wanted to do.

Fast forward eight years and many relationships later, and I’m now a trained dating and relationship coach. This year I texted the man I’d been dating for about a month: “Can I share a desire?” He replied, “Yeah, of course, what is it?”

“I want to spend Valentine’s Day with you this Friday night and I really want to go to this restaurant, The Little Prince in the West Village.”

He replied back just a few minutes later with the link for the Open Table reservation he made for us with a smiley face and typed “Done.” He then texted, “I want us to dress up.” Together we co-created the experience and had ourselves an amazing, connected night, despite the below freezing February NYC weather.

I knew that because we had just started dating and still didn’t know each other too well, he might feel at a loss for how to plan an evening that already had so much societal pressure. Maybe he’d ask his coworkers for advice and get a bunch of random suggestions from other people. Ultimately, I decided to not leave it up to chance. I wanted to help him win. I knew that expressing my desire clearly from a genuine place of excitement would bring much more pleasure and electricity into our connection than the awkward guessing game and feelings of unmet expectations.

“Molly, what you’re saying just feels really vulnerable,” a woman said to me recently.

We were in a small group and she and another woman asked me, “What is the biggest area you support women in? What’s the most common struggle you see for women in early dating?”

It was an absolute no brainer.

As a dating and relationship coach, I now witness from the other side women struggling in their love lives because a) getting clear and honest about what they really want and desire is courageous and hard work; b) owning and approving of what they want in the face of societal conditioning is extra challenging; and c) clearly communicating said desires in the throes of an intimate connection or in a new relationship can feel vulnerable without the right tools and skills to help increase confidence.

To her, the idea of explicitly expressing exactly where she wanted to go for dinner, or exactly what she was looking for in a relationship, made her feel extremely vulnerable.

It can’t be stated enough: In order to have healthy, sustained relationships, we must be able to properly communicate.

Having a backbone and being able to openly and honestly communicate our needs and deeper desires is what gives our partners the ability to win with us. Otherwise, it becomes a game of navigating ambiguous and potentially frustrating expectations and assumptions where a lot of times, no one wins.

Here’s the truth: They can’t read your mind. One more time for the people in the back: They can’t read your mind.

It’s easy to forget, especially in the early stages of dating. At first, we’re excited by the possibility of having met the perfect person. Everything feels new and exciting. The ultimate love story still seems possible. You know, where they show up for the first date and sweep you off your feet with the evening of a lifetime. Where they plan it all perfectly, knowing precisely what it is you want in every possible sense.

When I coach my clients, often in the midst of their disappointment that this isn’t happening, I almost always hear myself saying the same thing: “They can’t read your mind. You will have to let them into your inner world. Make sure to tell them what you like, where you want to go, and what you want to do.”

That’s when I usually hear something like, “But that isn’t romantic at all! I want someone who just knows what I want! Who shows up with the bottle of champagne and takes me exactly where I want to go.” Well, maybe it’s not “romantic” to have to share and express our desires outright, but truthfully, to expect otherwise might be a bit delusional, no?

Give them a chance

The longer you get to know someone, the more of an opportunity they have to get to know you and how to be a good partner. They will eventually learn and pick up on exactly how you like things, as well as the places and experiences that will make you happy.

The greatest benefit to being open and honest early on is discerning whether or not this is the right person for you. The ultimate test is their reaction. If they are welcoming and well-receiving of your expression, truth and desires and encourage more from you, then they are likely someone that can withstand what it takes to really have an open and honest relationship. And if not, if what you want or express has you feeling like “too much” or isn’t in line with who they are, then you don’t have to waste your time and risk finding out later, the harder way, that this probably wasn’t the person for you.

“Okay, Molly. That all sounds great, but what if I don’t know how to do that? I don’t even know if I could get the words out if I tried to do what you’re saying.”

Whether you are in a serious long-term relationship or are just getting back out there learning how to navigate this new world of dating and connecting, there’s no wrong time to start asking for what you need and want. In all truth, they’ll appreciate it just as much as you.

Here are some tips to get started.

Ask permission

This may seem odd, but in my opinion, this is the most underutilized communication tool in relationships. I use it and love it; it has been a total game-changer for me. When we feel vulnerable or like we may expose ourselves—either by sharing something uncomfortable or asking for something we need or want—we might feel nervous, anxious, or exposed. These feelings can lead to thoughts like: What if I say the wrong thing? What if they’re completely weirded out and never talk to me again? What if they disappear and I get hurt again?

When there is something uncomfortable I want to share or ask or express my needs in some way, I found it works well to ask a question like, “Can I tell you something?” or “Can I share a desire with you?” It’s something you can use for anything — whether it’s to tell someone your favorite food or to bare your soul.

This is a helpful tool because:

a) It grounds you. Before you’re about to offload a bunch of sensation in your body in the form of a desire or truth, you’re giving yourself a chance to get present and be in your body. You’re less likely to get knocked by their response or lack of one if you’re actually in the moment and not spinning out on the ‘what ifs’.

b) It also allows the other person to gather themselves and give you their full attention. Nine out of 10 times, the response is, “Of course! What’s up?” You’re ultimately setting yourself up to win because you just got a positive response back which will likely ease some of those nerves. If the response is “Yes, I’d love to hear but I’m running into a meeting. Can I ping back when I’m out?”, then you know when they reply back they will actually be present to hear and receive what it is you want to say. I love using this tool. Our partners want us to be happy and they want to experience that joy and fun alongside us too.

Ask from a place of believing they will say yes

This is a really big one. There are two ways that our beliefs can interfere with us having the relationship we really want and deserve.

First off, it is a totally normal thing for us to be carrying around baggage from our old relationships. As time goes on, as we gain more relationship experience, we may also pick up all kinds of negative ideas about how men and women are. We do this to protect ourselves from feeling those same rejections, anxieties, and disappointment. The same pain once again. The challenge we face, however, is not allowing that same need for protection to keep us too protected. If we’re too careful or too defended and play it too safe, these pains of the past can interfere with having the relationship we really want and deserve in the future.

Second, maybe you’ve been told in the past, that you’re too much to handle, not interesting enough, too needy, etc. Maybe you believe that you’re not deserving of a happy, healthy relationship. Walking into a new relationship with these beliefs, there is no other outcome possible but to have those experiences again. We are hardwired to walk right into what we believe, what we know, what we have had in the past, not what we want. That is just the way the subconscious mind works. The sooner you understand and accept it, the sooner you can change it. Ask from a place of believing they will say yes and want to be in service of what you want and need. My entire dating life changed when I worked on believing that:

a) I was an interesting and dynamic person that people wanted to spend time with and get to know.

b) People really wanted to help and support me to have all the things I wanted and desired.

A belief is a thought you keep thinking. If you really want to have the relationship you desire most, take the time to look at your beliefs.

Decide what beliefs serve you better and begin to focus on them. Rehearse them. Recite them over and over again in your mind.

Whether you’re currently in a relationship or just getting back out there dating again, it’s never too late to start.

Be willing to take a risk

Yes, you will have to take some risks and put yourself out there. Staying in our comfort zone all the time might be comfortable, yes, but that is not where the payoffs and depth of experiences come from. We wouldn’t really have growth and expansion if we didn’t take some risks. I find myself saying this a lot to clients: “If they’re scared away by your directness or honest communication, then it isn’t a good fit! Now you know and can move on to find the right fit.”

The right, secure person will welcome and want your openness and honesty. They will want to be a contribution to the things you want. They will take responsibility or ask for clarity and help and understanding if there’s been a miscommunication. They will want to repair the connection and do better. They will hold space for you to express yourself and meet you with patience and kindness. They will want to feel the full range of your desire, expression, and range of emotions. They will want all of you.

Yes, these people do really exist, I promise, but you won’t find or get closer to finding them without first standing up for what you want and deserve.