How to Stop Fearing Rejection and Start Dating

The fear of rejection holds many people back when it comes to dating. Fear of rejection is a debilitating feeling that stops many people from connecting with a person that they find attractive and interesting due to the possibility that the other wouldn’t share the same sentiments. To avoid hurt and disappointment many people choose to suppress their desires and succumb to their fears. But not trying doesn’t get anyone any closer to what they would like to achieve. To learn more on the matter I have met with dating coach Amin Lakhani. We discussed his personal experience with dating and his approach on how to deal with fear of rejection and start dating.

Amin Lakhani graduated from The University of Pennsylvania with degrees in computer science and economics (from The Wharton School) and is a former Microsoft employee. After working through his own challenges in the dating arena and watching his friends struggle in that same field, he decided to make it his life mission to help other men succeed in achieving the relationship they crave. To learn more about him and his services you can visit his website The Dating Coach on Wheels.

What was your initial experience with women and dating?

I grew up being very successful academically, however I was dead last when it came to relationships. I didn’t know how to date. I was interested in girls, but I had no idea how to further that interest in them, or even how to talk to them. I was also afraid of rejection. I was unsure whether a woman would be interested in me, because I have a disability and I use a wheel chair to get around. I also didn’t know anyone who is like me and who successfully dated women. As a result I focused on school, assuming that if I have a good education, become successful and wealthy, have a nice home, and a nice car, maybe then women would like me. I went to the University of Pennsylvania in Philadelphia and earned two degrees: one in the school of engineering in computer science and another at the Wharton school of business. After graduating I got a job at Microsoft and moved to Seattle. I had all those achievements but there were no girls to be found. I lacked confidence, I lacked prior experience. I thought having a relationship was just going to happen to me. I thought that when I got to a certain point in life the girls would be knocking down my door, but that didn’t happen.

What did you do to change your reality in the dating arena?

I looked into a lot of online resources. There are so many online resources for guys on how to be better with women. Unfortunately it is mainly focused on physical things – how to have sex with women.  And yes, that was of interest to me, but not what I really craved. I honestly wanted just that one girl that I’m really connected to, who likes the things that I like. I really wanted that connection. When I was 23, I came across a dating coach here in Seattle who was giving a seminar titled “conversation secrets.” I thought that was a great place for me to start, since I couldn’t talk to women. I couldn’t hold a conversation for more than 10 seconds and not freak out. I went to his presentation, and thought it was very helpful material. He seemed to know what it was all about. I approached him afterwards and asked about his private coaching. At first he wasn’t sure about me; he had never helped a man in a wheelchair before. He thought about it for a few days before he agreed to work with me. It was a life changing experience.

What did you learn from him?

Three basic principles:

1.     I get to decide how people see me. I was dressed like a sad guy and I didn’t really make eye contact with people. I would try to get out of people’s sight as soon as possible. He said, “Well if you are acting like a sad shy guy in a wheelchair - that’s how people are going to treat you. Yes, you stick out; you look different. You either try to hide it, which is not going to work - you are still going to be noticed, or you just own it, and say, ‘OK, this is who I am, and I’m going to give people something to look at.’” So I changed how I dress.  He gave me some pointers to start off with, and from then on I really picked it up on my own as I started taking interest in fashion. I started getting a lot of compliments.

2.     Connecting with people by being genuinely interested in them. He made me read How to Win Friends & Influence People by Dale Carnegie. The premise of this book is that you need to be genuinely interested in other people. Before, I used to think I had to do awesome things in life to get people to be interested in me. That might help, but ultimately it comes down to how comfortable people feel with you while talking about themselves. If you get people to talk about something that is deeply important to them, they will love you. People are dying for that focused attention – when a person asks them questions, listens intently, and internalizes what they are saying. That is a great gift to give someone.

3.     Having courage. I’ve always thought women like strong built guys who can lift them up and carry them, like the knights in shining armor in the movies. I was right that women do like strength, but it’s not just about physical strength. What is more powerful and shows more strength is having the courage to tell a woman that I find her attractive; to have that courage no matter how many times I had been shut down by other women in the past. It is a scary thing to open your heart knowing there is a chance that you might get rejected. We are hard wired for that rejection to hurt. And it does hurt. It’s about finding ways to process those feelings and doing that again, despite the pain of the rejection. For me, my coach said, “I’m going to be honest with you, 95% of the women in the world, maybe even 99% of the women of the world, will write you off before you even have a chance. The question is - are you going to talk to those 100 women to find that one who will be open to it, or are you just going to quit if it doesn’t work out with the first few?”

How did you become a coach yourself?

I really enjoyed my time at Microsoft, but due to health problems I decided to take a leave of absence.  In that time I thought about what I would truly want to do in life. Initially I just wanted to be a public speaker, which I still do and enjoy. I thought about what other skills I have – and coaching just seemed like it was calling to me. I wanted to help people with their struggles in the same domain that I’ve struggled.

Who is your clientele now?

My clientele is typically men in their 20s in the tech sector. Guys in technology, like myself, are bred to be good with computers, which is completely the opposite of how humans work. It’s like sciences versus art. We are very left-brained, and we struggle in relationships because you have to use your right-brain to connect with people.

What are the most common issues your clients need help with?

It relates to the three points I mentioned earlier. They aren't aware of how their appearance is perceived, they struggle to carry a conversation, and they don’t have the courage to let a woman know that they are interested in her. They are so scared of rejection that they don’t put themselves out there with women, or don’t do it enough. They are waiting for the girl to make the first move. In some cases they have that one girl that they already know and have their heart set on; they really want something more with her but lack the courage to actually let her know.

What advice would you have for a man who is attracted to a certain woman, but has not been able to approach her?

Just go and talk to her. Make sure you are dressed well and engage her in a conversation.

Many guys, and even women, make the mistake of trying to suss out a lot of signals to know whether or not the other person is interested. It is way easier if you just let them know that you are interested and move things forward. You can say, “Hey, I think you are super cute, you are really fun to talk to, and I would like to take you out on a date.”  Very simple. Their answer will let you know everything you need to know. It is scary, because not everyone is going to say yes to that. Sometimes people think, “Oh, maybe she needs to know me better.” But that is how you get to know the person better - when you go and hang out with them. It’s not going to happen at work, it’s not going to happen amongst your friends. You need time alone. In reality, I believe most women have already decided if they want to go out with you before you even say a word. So conversation is good; it’s good to know more about them and make them feel more comfortable in making that decision of going out with you, but ultimately it’s more important to just pull the trigger and ask her out.

Some guys index on trying to build the connection first.  They meet a girl, talk to her at length, but they don’t ask for her number because either they don’t feel like they know each other well, or they are with friends and don’t want to seem weird.  Once they go their separate ways it becomes a missed opportunity. Who knows if they will meet that person again.

How do you train a person to get over the fear of rejection?

The reality is that you never get over that fear, because it’s hardwired in us. All you can do is to do it anyway, over and over again. You learn to be vulnerable, as Brene Brown wrote in her book Daring Greatly, and do the work to heal your wound. Sometimes there is a long stretch of time where things don’t go anywhere. And it’s really taxing. You need to share this experience with someone who loves you no matter what. It can be family or friends. You need to talk about it and get it off your chest and feel accepted. You need to build a community around you that is going to support you in what you are doing. I have a close network of friends that I know whenever I don’t feel good I can call them up to talk. When I go through a tough time, they are there to listen and support me and build me back up.

Can you share a success story?

As part of my in-person sessions I take clients out to places like the mall, coffee shop, or book store and I have them practice going up to people and starting a conversation while I observe and later give them feedback. One of my clients, when he first came to me he couldn’t maintain a conversation at all. He could hardly talk to me. The idea of going up to a woman and starting a conversation was horribly terrifying for him. We did a lot of work and a lot of exercises on how to come up with things to say and how to genuinely connect with people. One day, we had a session in which he had talked to 15 women over the span of 2 hours and it had gone nowhere. Every woman had shot him down. All the conversations were 30 seconds of less. He was really struggling that day but agreed to try one more.  We got out of the elevator, and without me telling him a thing, he just went towards this girl, whom, later he told me, he thought she was very attractive, and he talked to her for 20 minutes and got her number. When he initially asked for her number, she refused; she said she doesn’t give her number to strangers.  So he stuck with it and genuinely got to know her. He got back to those skills of getting to know a person. That’s what I teach my clients. It’s not about just getting the number; it’s about brightening someone’s day and creating a genuine connection.  It felt really good to finally see him get to that point.

If you were to coach women on dating, what would you advise them?

To bear in mind that guys tend to think that women have all the power to drive the success or failure of their love life: the guy offers and it’s up to the woman to say yes or no.

If you are not interested don’t lead him on. Don’t say yes because you feel like being nice. Be kindly honest: you can say, “Hey, I really appreciate it. It’s really courageous, I encourage you to keep doing this, but I’m not interested.”   This way he can move on to someone who is interested. He deserves someone who is genuinely interested in him.

If you are interested, guys really appreciate it when a woman takes more initiative and gives them some sort of sign or encouragement that she would love to hang out with them. Initiative has got to be used sparingly; if a woman starts to take all the initiative it could be a huge turn off for a guy.  Guys do like the chase; it’s just like everything in life – if you don’t work for it you don’t appreciate it. 

I usually tell guys to plan the date and pick the day and location. If a woman is still interested in going out with him but the time doesn’t work for her, it would be nice if she offers an alternative instead of just saying the time doesn’t work for her.

On the first date – don’t talk too much about yourself. Make sure it’s a balanced conversation between the two of you. It’s your opportunity get to know him better. You want to avoid the type of conversation when one person is quiet and the other person talks and it becomes some sort of a therapy session.

If you get food and drinks – offer to split it. Usually the guy will get it the first time, as is the general custom, but it’s always nice when the girl offers. 

Don’t plan something else on your date night. It may be nice to have a backup plan if the date falls through, but then you don’t give yourself a chance to really get to know the person and see where it may go. If you really need to go somewhere that night, let him know in advance - so he is not caught off guard; he might have something grand planned for you but if you just cut it off last minute, that leaves a sour taste.

It would be nice if on the second or third date, especially if the guy says that he would like to see you again, if you offer where to go or what to do the next time you go out.  I think if a girl takes the initiative and says, “hey, I really want to go with you to this thing.”- it makes a guy feels really good. It tells the guy that you really want to spend time with him and that you are not just saying yes because you’ve got nothing else to do.  It tells him that you actually think about him and enjoys his company. That makes a world of difference.


  1. This is really good post and these tips mention in your post will help many people to maintain their relationships.


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