How to Transition into Personal Conversation the Easy Way

by Eric Disco
Jan 25

This post is from Hurricane Lee.

You can approach girls. You can ask for the time. You can ask for directions.

You can ask a few related follow-up questions

But you can’t transition into a personal conversation.

Sounds familiar?

You are not alone. Everyone starting out in game has the same problem.



Because it reveals the most fundamental fear of all: the fear of judgment.

That is what’s going on in your head. You are afraid of being judged inadequate.

While you are asking for the ordinary, no one is judging you. But when you transition to reveal your interest, you are being judged by the girl you approached.

There is no way to stop this from happening. You have to get used to it happening.

The solution to this problem is to make the next step very, very small. Instead of diving right into a personal conversation, stretch that process out into two or three additional steps. Get used to each step individually before moving on.

Recently, I had success giving the following advice to a coaching student.

After directions, make an innocuous comment. I like:

“Thanks for the help. This is a very friendly city.”

Now, repeat that again and again until you are making that comment each and every time you’ve been given directions.

After the comment, no matter how friendly a reaction you get, walk away.

Next, extend the comment by adding a question:

Thanks for the help. This is a very friendly city. (Small pause.) Do you agree?”

Wait for her to agree or disagree, but no matter what she says, smile and walk away.

Do it again and again and again until you’re comfortable.

When you’re ready, add more:

“Thanks for the help. This is a very friendly city. (Small pause.) Do you agree?”

(Allow her to respond.)

Then add:

“You know I have this friend. When he sees people on the street or on a subway eating, he will ask them ‘Can I have the last bite?’ You know what’s amazing? No one says no. People are a lot nicer than we tend to give them credit for.”

Again, get used to this step by repeating it again and again and leaving when you are finished.

Finally, when you are really ready, the next step to a personal conversation is easy.


Because you’re already chatting about the city and how friendly everyone is.

There are several ways you can go, but the easiest is: “Where are you from? Are you a native of my beautiful city?”

That’s it. You are now in a personal conversation. And you’ve gotten there without making any big leaps.

- Hurricane Lee


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posted in Initiative and Inhibition, Rapport Skills

21 responses
Samy says:

Lee, very helpful post.

Actually, my problem is slightly different … I came across someone through my work and really liked her (unfortunately, we are not in the same city, but there is a good chance I will move to her place in the next few months).

Would you have any ideas for me on how to make the transition from professional to personal talk? (Also, I have no idea if she is already in a relationship or not.)


Eric Disco says:

The best way to make this transition is to talk about yourself. Lead the conversation into personal territory by going there yourself.

When you see her on Monday, ask her how her weekend was. If she talks about her weekend, awesome. Most likely she’ll say, “Good. How was yours?” At that point you can talk about something you did. “I went to a yoga class. I was terrible at it! You do yoga?”

This way you’re getting personal, but you’re not prying by asking her personal questions. Particularly if you’ve known her for a while at work and not gotten personal, personal questions will come off as weird.


Lee says:

I agree with Eric. When you share something personal, you are allowed to ask about the same. Don’t chat too long. Just a few minutes. You don’t want to be the chatty co-worker who overstays his welcome. When should you ask her out? When she’s asking you questions about yourself. When she does this on a regular basis, ask her out. But do it in a way that gives her the opportunity to politely say no. “Hey, next Tuesday, after work, I’m going to head over to Blah Blah Blah Bar. It’s just a few blocks from here. Supposed to have the best margaritas in the city, and I’m a big fan of margaritas. You should tag along.” If she’s not interested, she’ll say she’s busy. If she’s interested and busy, she will also offer an alternative. “Hey, I can’t. I have to meet my cousin for a dinner on Tuesday, but I’m around all of the following week.” Something like that. If she offers no alternative, don’t push it. It’s a work environment and you have to see her every day.


Samy says:

Good points, Eric and Lee.

Actually, my problem is complicated by the fact that we only interact over email and Skype (we are in different cities, but there is a strong chance that I may move to her town in the next few months).

Would you have any ideas on how to ask for her cell number and a time to talk with her in the evenings? (Or is this all too much of a long shot?)

Thanks a ton!

Lee says:

I would give up on this one, buddy. There’s too much going against you.


Samy says:

Yeah, that thought did come to me. Its just that am part of an ethnic minority and there are very few people like me (the girl in question is originally from my country).

Online dating is very frustrating. I wanted to try and see if I could convert this small chance into something …

Lee says:


As I once wrote in an article on this forum, perceived similarities are not the reason two people are attracted to each other, so looking for those perceived similarities as an easy way in is not going to help you. In general, every new encounter is a low probability bet, so rather than spending a lot of time on something that is likely to be a bust, you should teach yourself to approach other women.


whatever says:

Seems to me these guys are bailing too fast.

The obvious discussion topic to approach her with would be your pending relocation–you can ask her about how it is living in her town, since you may be moving there. She would expect that innocent conversation from anyone.

That leads pretty directly to her potentially showing you around some time when you’re in town.

Manray says:

I see more and more parallels between sales and pickup. Yes, you work on your wardrobe, your pitch, building rapport, and closing the deal. And, like in sales, you have to keep going from no to no with no loss of enthusiasm.

Most sales conversations also lead to a no, even for the worlds best sales people. But it only takes a few yeses to make the nos worth it!

Lee says:

I agree. It’s sales. First, you have to believe in the product. Then, you have to present the product in the best way possible. Finally, you should get used to rejections. What are the chances that you choose to approach someone exactly when they want to and can buy your product?


Samy says:

Lee, thanks for your reply.

Inter racial relationships are far and few and I hear that they don’t work out in the long run. Would you recommend any blogs or material that deal with them?


Lee says:

Yes, I did read some studies that interracial marriages have a higher divorce rate, but this shouldn’t change your strategy. You should learn to approach girls that you are attracted to, wherever you are. If those happen to be girls of the same race, you have to move to a place where more of those girls are available. Focusing all your attention on a long, long shot just because she happens to be of the same race is not going to get you what you want. Any one girl is a low probability bet. You have to hone your skills and meet lots of girls to maximize your chances.


Samy says:

Lee, good points.

I have a background in doing research and am into eastern philosophy (meditation, minimalism & spirituality). I am looking for some one who is good looking and has some overlap with my background and my interests.

What places/cities do you think would be good to find someone like that?

Thanks for all the help!

Chicago Definitely. Lots of those types here, however I’m willing to bet LA has a lot of that stuff too, probably more than a lot of places.

Samy says:

Thanks for your input!

Lee says:

Are you in the US? I am not an expert, but it sounds like big urban centers would be your best bet. New York, Los Angeles, San Francisco. These are places with both, the level of education that seems to be a match for your interests and a comfort with alternative lifestyles. Where I live in New York, yoga studios and meditation centers are all over the place.


Samy says:

Thanks Lee, I have found you replies to be very helpful and encouraging.

I wanted to discuss with you some more about my situation. What would be a good way to do so?

Just a Guy says:

LA for sure when it comes to Eastern Thought. There’s a huge place on Sunset near the beach, I think it’s called …can’t recall. It’s centered on the teachings of Paramahansa Yogananda. Topanga Canyon also has lots of places in the same vein.

LA is weird, though. Having lived there for many years, the whole process of meeting women is an odd ordeal. Lots of girls who were the hottest in their respective small towns move to LA and get lost in a sea of other chicks with the same story. Strong bitch shields there – chicks get a ton of aggressive game from every guy imaginable – even homeless dudes! Not a lot of walking traffic, either. Santa Monica and Venice are about it, and Venice is freakville. I have met (and slept) with some spiritual honies thanks to the Bhodi Tree Bookstore on Melrose.

Yeah, you can meet women in classes, but Yoga is $15 a session and it adds up. And even then, people really keep to themselves. And while Whole Foods often sports some hotties, and you can sometimes meet some chicks there. The best place I found to meet women was in college psychology courses – chicks love psych.

Not much eye contact in LA, either. Actually, watch this vid of an older lady complaining about exactly that.

Socialkenny says:

This happens to me periodically.

As for transitioning, I think that a lot of guys get frazzled also when the girl doesn’t seem to be totally committed to stay and chat. At least on cold approaches.

Lee says:

Yes, that happens, but the true fear is not that a woman is anxious to leave. Her haste does not affect you. Just imagine yourself really asking for directions – meaning, you actually need directions. Suppose you didn’t understand something she told you and you ask a follow up question to which she answers “Sorry, I’m late. I gotta run.” And takes off. Do you really see that as a situation that causes you some anxiety? No. What causes you anxiety is judgement. She discovers that you have an interest in her and immediately judges you as worthy or unworthy. That is why transitioning in the way I describe above lowers the barrier. You say “Thanks! This is a very friendly city. Do you agree?” She nods and immediately takes off. Is that bad? No. So far, still no judgement. Now, what if she smiles, nods, and says with some surprise, “Yes, you’re right. It is a friendly city.” That is an invitation to keep rolling, so you do. Get it? There is never that point of a hard transition.


Mik says:

Great advice. A slow bit by bit approach is great for guys who don’t have that much experience. Thanks