A good coach changes the world. That’s what I learned from Rich Litvin and Steve Chandler’s book The Prosperous Coach.
Jacob was a longtime subscriber of mine. He reached out to me because he had never had a girlfriend before, and he wanted help finding a good woman who loved him and understood him. The two of us scheduled a free coaching session together. Even though we originally only planned to spend 1.5 hours together, our session ended up being two hours long. I didn’t mind going slightly over time. One of my principles is to always go the extra distance for a client—even the ones I work with for free.
During our coaching session, I helped him learn three keys to finding the woman of his dreams.
- Get ultra-specific on where you are, where you want to be, and how you are going to get there
- How to find the best places to meet women
- Exactly what to say to her to ask her out and get a date
Get ultra-specific on where you are, where you want to be, and how you are going to get there
To begin our session, I asked Jacob “What’s on your mind?” He told me that he wanted some help getting out of his head and back in the game. That’s an alright goal, I thought, but it’s a little vague. A good goal for Jacob needed to be much more specific. I asked him to tell me what he wanted to accomplish as a result of our time together.
Jacob explained that he wanted to overcome his stuttering and social anxiety. That’s a better goal, and at this point a lot of other coaches might have just given him some generic advice on how to be more confident and sent him on his way. However, I knew there was still room to get even more specific. I asked him a simple question that Michael Bungay Stanier writes in his book The Coaching Habit is one of the best coaching questions in the world, “And what else?”
He told me. Jacob explained that he wanted to find a woman who understood him, who cared about him, and who would eventually marry him. Jacob also told me that he was in his late 30’s and was at that point in his life where he wanted to settle down. However, he’s never had a girlfriend before. In fact, the last time he had been on a date or even asked a woman out before—was 11 years ago!
“Now we’re getting somewhere”, I thought to myself. In the beginning of our conversation when Jacob first told me that he wanted help getting out of his head and back in the game, it wasn’t clear to me at all what he wanted to accomplish. If all he had was a generic goal, then all I could offer was generic advice. After getting ultra-specific on where he was and where he wanted to be, we are now able to come up with ultra-specific action steps that would take him there.
I asked him to brainstorm a few ideas on what action steps he should take. Jacob suggested that he could try meditating. Perhaps he could try being more positive. “That’s a bit vague,” I told him. “What specifically could you do that would help you get where you want to be?” He started having trouble coming up with new ideas, but I couldn’t fault him for it since the last time he had been on a date was over a decade ago. I jumped in to help him. “If you’re going to find a woman that you eventually want to marry then there are two things you need to do. First, you need to come up with great places to meet women. And second, you need to talk to her and ask her out.”
At last, we had our specific action steps for Jacob.
How to find the best places to meet women
The first thing Jacob needed to do was figure out where he was going to meet women. Some coaches may have just given him a generic list of places for him to go and meet women, but I wanted to go the extra mile for Jacob. Before the end of our session together, I wanted Jacob to have three specific places that he could go to meet women.
To do that, we held a brainstorming session. Based on where he lived and what venues were nearby, Jacob and I came up with as many ideas as we could where he might meet someone. Our long list of possible venues included volunteering activities, work, the mall, Starbucks, the park, bars & clubs, and even cooking classes. Some of our ideas were good, a few of them were great, and several of them were just outright ridiculous! That was okay. Our plan was to generate as many ideas as we possibly could and then pick the top three places for Jacob.
For a potential venue to make the cut, it had to meet two criteria. First, it needed to be a place where Jacob could meet women. Second, it needed to be a place that Jacob would be interested in exploring. Bars & clubs are often thought of as a great place to meet women. However, Jacob was an introvert and going to those types of places just isn’t his thing. So, we axed that idea. We also considered cooking classes, but it turned out Jacob was not too interested in that either. The three places that made the cut were: ballroom dancing, online dating, and his church singles class.
Jacob told me that a friend of his regularly went ballroom dancing and that it was something he “always wanted to try”. In fact, there was a dance studio right in the area where he lived! Almost by definition, ballroom dancing is a wonderful way to meet a lot of women. It would also help Jacob learn how to be more confident and how to take the lead with a woman. If there’s something a woman loves, it’s a man who can lead and a man who can dance!
The next venue that made the cut was online dating. It’s a great place to meet women without even leaving your room! You can even filter by age, personality, hobbies, interests, etc. If you have a certain hobby and it turns out that she’s also into that same hobby, you may just have a match made in heaven. Jacob told me that he had never made an online dating profile before. There are a lot of options for different websites, but my advice to Jacob was to just pick a website and go for it. If you’re not getting good results with one website, then you can easily just switch to another. (However, if you’re not getting results with any website then your profile might need tweaking). I’ve personally used OKCupid to great effect. Alternatives include Plenty of Fish (free) and Match.com (paid).
Finally, the last place we decided on was a church singles class that Jacob regularly attended. It was even separated by age! At the class, there were people in their 20’s, 30’s, 40’s, and so on, all sorted together. My jaw dropped when he told me about this. “Wait a minute,” I asked him. “You’re telling me that there’s a class you regularly attend, with a bunch of women your age, who go to the same church, and you KNOW that they’re all single? Dude! You need to get on that!!” Sometimes the best places to meet women are right in front of our eyes.
The exact words to ask her out and get a date
At this point, we’ve gotten ultra-specific about where Jacob was and where he wanted to be. We’ve also decided on his top three venues to meet women. The final piece of the puzzle would be for him to talk to a woman at one of these locations, ask her out, and then get a date. I wasn’t leaving anything to chance. Before the end of our session, I wanted Jacob to know exactly what he was going to say to her and to have practiced it enough times until he could say it with confidence.
“Jacob,” I asked, “imagine that you’re talking to a woman. It’s going really well. The two of you are hitting it off. You’re interested in asking her out. What might you say to her?”
“Umm…would you like to go out on a date?” he replied.
It was a start, but there’s room for improvement. I asked him to try again.
“Umm…I could ask her what food she likes…and then ask her out to that.”
We’re getting there! I told him to try again, but this time adding a specific time and place. He gave it one more try…
“Would you like to go ballroom dancing with me at [name of local dance studio] this Saturday at 8pm?”
That’s it! The key is to ask her out to a specific time and place. When you’re asking her out, you want to make it as easy as possible for her to say yes. If she’s interested, all she has to do is say one word,” yes”. If you don’t have a time and place in mind, then it puts the burden on her to come up with a time and place for you. That creates additional busywork for her. If she has to jump through hoops to go out with you then it makes her much less likely to do so—even if she was interested in you in the first place!
Okay, you might be thinking, but what if she’s not available at the time you proposed? What if you ask her out to go ice skating with you next Saturday…but she already has plans to go shopping with her girlfriends that day? Here’s the thing. If she’s busy during the time picked, but she’s still interested in you, then she’ll probably let you know. She might propose an alternate time for you to go out. Or, she might let you know what time she will be available.
Finally, what if you don’t know what she likes to do? This is something that also held me back. What if you ask her out to dinner at an Italian restaurant…but it turns out that she hates Italian food? It turns out the answer is much simpler than you might think. Just take your best pick at what place or activity the two of you would enjoy doing together, and if she doesn’t like that idea, she’ll let you know. Sometimes she’ll even pick an activity for you. My suggestion is to ask her out on a date that centers around a fun activity that the two of you can do together, such as mini-golf or bowling. (Between you and me, ice-skating gives you a great excuse to hold hands. I’m just saying!)
Let me tell you a secret…
Okay, I want to tell you a little secret before I go.
When Jacob told me about his dating situation—that he was in his late 30’s and had not been on a date in over a decade—my first thought was “Oh, crap. I’m out of my league.” I suddenly began to doubt myself and I began to wonder whether I was truly capable of helping him. However, once we started working together to come up with places and scripts to interact with women, I felt my self-doubt melt away. We had an amazing session and Jacob wrote me afterwords thanking me for my help after it was over.
Sometimes I hear men tell me that they feel they can’t get a girlfriend. “It’s too late” they because they’re in they’re late 20’s or even late 30’s. “I’m too ugly”. “I’m too uninteresting”. Etc. I want you to know that, whatever your situation is, there’s no reason why you shouldn’t be able to find the woman of your dreams. Just take a look at Jacob. If someone in their late 30’s who’s haven’t been on a date in over a decade can do it, so can you!
To make it super easy for you, I’ve prepared a FREE “How to Talk to Women” conversational cheat with exact words to talk to her, ask her out, and get a date. Enter your email below and I’ll send it straight to your inbox!