Ask the Date Boss- Being the Other Woman

Ask the Date Boss: The Other Women

Dear Date Boss,

I am in a relationship with someone who has a wife and 5 children.  I believe him when he tells me that he loves me.  He tells me that he is going to leave his wife and children for me but the timing isn’t right.  I believe him.  Something isn’t right though.  Anytime he is with his wife and children and I try to text or call him, he never picks up his phone and never returns my text messages.  Help!

The 2nd woman

Dear 2nd woman,

What exactly are you looking for in a relationship with someone who has a partner and 5 children?  What are your expectations? Are those reasonable expectations to have with a person who is married with five children?

If you are falling for the line, “I am waiting for the right time to leave my partner…” then you need to wake up.  He may want to spend some time with you, he may want to have sex with you, but that does not mean that he wants to talk to you 24 hours a day, 7 days a week nor does that mean he wants you to replace his wife.  The man that you love is keeping family time to family time and his girlfriend time to girlfriend time.  You are the woman on the side.  You are the 2nd woman and you are being treated this way.  He is keeping them separate for a reason.  It could be that it allows him to feel cleaner about the situation.  Maybe he doesn’t want to be connected to you in his ‘real life.’  Maybe he loves the thrill of keeping you a secret.  He doesn’t want to be reminded that he’s having an affair while he’s having dinner with his wife and children.  That would just make life more complicated for him.  Who knows if you are even his ‘only’ girlfriend?

To resolve this issue that you are having, find a person who meets your expectations and is not married.  This one appears to be taken.

If you have any questions that you want to ask, shoot me an email, hit me on facebook, comment below or on twitter @TheDateBoss.

Posted in Home

Ask the Date Boss: Going from dating to being exclusive

Dear Date Boss,

How do you know when you’ve moved from dating to exclusively dating?  How much time should elapse and how do you approach the subject?

Soon to be Serious Sarah

Soon to be Serious Sarah,

If you haven’t read my post about THE RELATIONSHIP TIMELINE, check it out here!  It’s an information filled post that discusses a general relationship timeline.  As for your first question of “How does one know when you’ve moved from dating to exclusively dating?” the answer is that you will know.  I define exclusively dating as solely dating one person.  You will know that answer to that.  Are you dating only that person?  Now, if you are in an exclusive relationship, then your partner will only be dating you as well.

Now how do you approach the subject and when do you have ‘the conversation?’  “The conversation” where you define what your relationship is with your partner will vary from case to case.  It’s a matter of what your expectations, as well as your partners, are.  You will have this conversation when you feel the moment is right.  When it starts to creep up on you and you want to know where the relationship is going, then that is the right moment to have that conversation.

This feeling can happen the moment you meet, a couple dates in, or months after you have spent time together.  As you spend more and more time together, you’ll begin to wonder “where is this relationship heading?”  “Am I where I want to be in this relationship?”  “Is this what I want?”  As I’ve said in a prior post, define what you feel and what you are looking for in a relationship.  When you have these questions, it’s time to stop being ambivalent and really solidfy your thoughts about the relationship.  Assess where you are in your relationship, what you want and what your partner is looking for.  Discuss your expectations.  Own up to what you really want and stick to it.  At the end of the conversation, at least you will know where you stand.


If you have any questions that you want to ask, shoot me an email, hit me on facebook, comment below or on twitter @TheDateBoss.


Posted in Blog, Home

Ask the Date Boss: I’m 20. Should I be in a Relationship?

Dear Date Boss,

I’m 20 years old college student that is currently studying abroad. I’m also in a long distance, on again, off again relationship. So I met this handsome, charming man that would make me laugh non-stop. I couldn’t help but smile when I was with him. I’d get butterflies in my stomach and I wanted to spend more time with him. I started to feel guilty because of my ‘complicated’ relationship. Should I even be in a monogamous relationship at this age, nonetheless, a long distance relationship?

Marketing Major in Madrid.

Marketing Major in Madrid,

There are two issues that I’d like to address.

1) Should you be in a monogamous relationship at the age of 20 years old? This is truly a matter of preference. I will give you some food for thought. Relationships are between two people. You and your partner. With that said, you are young and you are still growing. What you know and like now can be much different than what the 30 year old, 40 or even 50 year old you would know and like. Change is inevitable. The bottom line is whether you are 20 years old, or 50 years old, are you willing to grow and change with your partner? Are you willing to go through the high times and the low times? Are you willing to make sacrifices to grown together or apart? Age isn’t the issue. Are you willing to fully commit to the relationship that you created with your partner? Are you willing to work for it?

2) Distance. Proximity. Research has shown that distance between partners can have a significant effect on a relationship. A short car ride. Great. An hour away to see your partner, that can be tough. A 3 hour flight? It’s getting tricky. On the other side of the globe. Woah now. Not only does distance play a factor but now we are also talking about for how long. A few days. No big deal. A week. Alright. Three to Six months. There will be issues in the relationship. Face to face, physical interactions are tough to come by. The physical touch between two people is very important. Knowing that your partner is just around the corner and you can be held brings comfort to a relationship. There is also the issue of time schedules. You could be 8 hours ahead/ behind of your partner. How will you commitment? Adjustments need to be made. Are you willing to adjust to the distance? Are you willing to adjust to knowing that you will not be able to hold this person in your arms for an extended period of time? Are you willing to adjust to the time differences? Are you committed to the relationship?

After thinking about these questions, I’m sure you’ll be able to make an informed about any relationship that you have in the future.

Best of Luck


If you have any questions that you want to ask, shoot me an email, hit me on Facebook, comment below or on twitter @TheDateBoss.

Posted in Blog

The Moment is now

This post should be read after reading my previous post, found Here!.

After thinking deeply about when opportunity, I’ve come to the conclusion that people are limiting themselves.  People are not taking opportunity when it arises, because they are stuck in the head.  A theme that I continue to hear over and over again is that the moment is not right.  The moment isn’t perfect for me to take that chance.  The moment isn’t right for me to do XYZ.  Countless times, I’ve heard people stalling and not taking the chance.  Not taking opportunity.

I have news for you.  There is rarely, if ever, going to be that perfect moment.  The stars will not always align when you have that opportunity.  There will always be something that you will be doing, or something that has your attention.  Suddenly, there is an opportunity to meet someone, do something together, and socialize.  There are many dating and relationship opportunities.  If you always have to wait for the perfect moment to act, you will never BE.  You will rarely act.  BE here.  BE now.

A perfect example of this is the coffee shop scenario.  While walking into a coffee shop on my way to work, I notice a beautiful woman who is working on her computer.  She is heavily focused on her work and she looks like she doesn’t want to be bothered.  Here is an opportunity.  Here is my one opportunity with this specific person.  Who knows if I’ll have another opportunity like this.  What am I to do?

Clearly, there are many issues that could be going on.  I’m on my way to work and have to be there at a specific time.  I may or may not have some work issues on my mind.  I may or may  not have some personal issues on my mind.  She appears to be working on something important.  It looks as though that she does not want to be bothered.  I have no clue if she has something on her mind either.  There are so many factors here that make this situation, not the perfect moment.  Do you step up to opportunity when it presents itself?

Another issue that I keep coming across is people waiting for their life to be perfect before taking a chance.  I am not saying that you need to be dating or be in a relationship.  You should date when you feel like you are in the right mindset and space to meet other people and possibly have a relationship.    Here is something that you should really consider though- Are you making excuses for not taking the opportunity of meeting and dating or are you really just holding yourself back?  There’s a thin line between making excusing and having valid reasons not date.

Here are a few things that I’ve heard people say.  Which ones do you think are valid reasons?  Which ones are excuses where people are holding themselves back?

  1. I’ll start dating once I’m back in shape.
  2. I’ll start dating once I have my finances set.
  3. I’ll start dating when I get that new car/job/ house.
  4. I’ll start dating once I’m over my ex-girlfriend.
  5. I’ll start dating when my schedule gets less busy.
  6. Dating is just not for me.

Statements 1, 3, 5, 6 are excuses to not date.  Statement 1 is an excuse.  Does a person really need to get back into shape to start to date?  No.  Would it help? It’s possible.  Statement 3 is an excuse.  Again, do you need it?  No.  Would it help? It’s possible.  Statement 5 is an excuse.  Your schedule should always be busy.  It will never get less busy.  That’s a fact of life.  As for statement 6, if you are reading this blog and say statement 6, you are just kidding yourself.  You want to date.  Stop making excuses.

Statements 2 and 4 could be excuses not to date but they could also be valid reasons not to date.  If a person doesn’t have a job or no income, dating could be difficult.  Having a steady income would be a great idea before trying to hit the dating scene.  As for getting over your ex-girlfriend, that could be a true statement.  Maybe you aren’t ready to go back on the dating scene yet.  Only you can tell if you are in the right mindset to start dating again.

Stop making excuses for yourself.  You will need to take action for dates to happen and for relationships to bloom.  Dating and relationships take work.  Successful relationships take even more work.  Making excuses and not owning up to your actions will make you unhappy in the long term.

You will rarely ever get a second chance at the same opportunity.  The moment is now.  The moment is here.  BE in the moment and act.  You’ll never know what will happen unless you act.

Posted in Blog

You deserve the best.

READ This Here- It has crude language.


A woman created an online dating profile w/ pictures of a model and had content that ‘touched on every major facet of being truly horrible: mean, spoiled, lazy, racist, manipulative, willfully ignorant, and…. a little gold digging…”  Results: She received 150 messages in 24 hours.  In response, she replied with horrible message that continued to portray this mean woman.  Yet she continued to receive messages.  Her conclusion: “Men of the world: You are better than this.”

Even though the article discusses men specifically, my blog post is directed towards both men and women.  The bottom line is that you, the reader, deserve the best.  You do not need to settle for someone.  There are many people in the world who are intelligent, kind, truthful and honest, and who will challenge you and make you want to become a better person.  There are people who will love you for being who you are.  There are people who will love you unconditionally.  There are people who understand that love is not about taking, but about giving.  These people will give you all that they are.  They will sacrifice for you.

You do not need to settle for someone who is jealous and insecure.  You do not need to settle for someone who will not let you have friends of the opposite sex.  You do not need to settle for someone who belittles you all the time.  You do not need to settle for someone who becomes physically or emotionally aggressive with you.  You do not need to settle for someone who will be with you because of your body.  Nor do you need to settle for someone who is with you because you have financial means.  Do not settle for anything less than you deserve.

You deserve the best.

Posted in Blog

True Confidence

If you’ve ever picked up any magazine in the supermarket and looked into the dating and relationship section, you’ve noticed that confidence seems to be a topic that is always covered.  These magazines talk about how confidence is sexy and how everyone is attracted to people who are confident.  Now, these articles are missing what confidence really is and how to have confidence.

People get confidence wrong.  Confidence is not about obtaining object of monetary value, looking like you can be on the cover of a magazine, being a medical doctor, or having a PhD.  American society has it wrong when they try to push those values on you in terms of confidence.  If you have one of those things, it does not mean that you will instantly have confidence.  They can be blocks to help you have confidence but they are not the keys.  Here is the answer.  True confidence is the ability to accept who you are fully, with both your strengths and faults.

That sounds so easy to do! It’s easy to accept myself fully.  I know I have my flaws.  I know I have my strengths.  I can recognize this.  But am I really okay with that?  Do I really accept myself with these flaws and strengths?  Am I self-conscious over these things?  When people take a real, hard look at themselves, not many are able to say that they are okay with themselves.

Now that you know what confidence is – self-acceptance- how, do you get it?  First, you have to earn confidence.  No one can give it to you.  You have to take it for yourself.  Secondly, you gain confidence through self-reflection.

When you practice self-reflection, there are many things that you need to think about.  I’ll briefly go over several highlights that will build the foundation for confidence through self-reflection.  First, acknowledge the fact that everyone has flaws.  No one is perfect.  Everyone has something that they are weak at.  Then, acknowledge your strengths.  An easy way to acknowledge your strengths is to look at your past achievements.   Are you a great provider?  Are you the first person in your family to get a high school diploma?  Write down these achievements on a piece of paper and write down what it took for you to obtain those achievements.  Were you creative, brave, courageous, a leader, humorous, fair, and persistent?  These are just a few of the varied strengths that people have.  After, take the time to acknowledge your flaws.  Again you must acknowledge the fact that everyone has flaws and no one is perfect.  What are some of your flaws?  Make a list.  Now here comes the most difficult part of this process.  Forgive yourself, let it go and try to improve yourself to move on.  There is a process to forgive, let go and improve oneself but I will go over that another time.  This will take the most time, effort, and be very difficult but will be the most rewarding thing you can do in this process. 

Once you are able to acknowledge that you have flaws and be comfortable with the fact that you are constantly evolving into the best person you can be, you will have a feeling of comfort within.  This doesn’t happen over-night.  There is no ‘ah-ha moment.’  This is a process that happens over time.  You will constantly be working on this process of forgiving yourself and improving yourself.  In time though, you will get to a point where you are truly comfortable with what you say, who you are, and what you do.  You will be completely congruent with your thoughts, feelings and actions.  Now this doesn’t mean that you will always stay at that point.  This doesn’t mean that you won’t be uncomfortable because you will be pushed from your comfort zone.

What confidence means is that you are able to accept yourself fully.  You understand your strengths and flaws.  You know what you are capable of, as well as your limits.  You are complete as a person.  You are an amazing being, even more so, with your flaws.  Confidence.  You do you.  You are okay.

Posted in Blog

Opportunity and How to Take it

In my previous post, I talked about how opportunity is everywhere.  You just have to realize this and you need to act.  Many people do not realize that opportunity is staring right at them.  Even if they do realize it, many people stutter and do not act.  Well, this post is about how to recognize opportunity and how to act on it.

Recognizing opportunity is not as difficult as one would think.  The most important step to recognizing opportunity is being open to it.  Be kind, courteous and friendly to others.  Be open to that random conversation, or line about the weather, or how the coffee shop is taking its sweet time this morning.  You can make a small comment about something you saw in the newspaper.  If someone is up for having a conversation with you, have a conversation with them.  If you feel uncomfortable at any point, stop talking, walk away or move to another place.

As cheesy as it sounds, did someone catch your eye and make eye contact with you?  Smile at them.  Are they smiling back?  Is someone laughing at your jokes, giving you compliments, touching your arm while having a conversation with you?  Does a person really need to say that they like you?  Reciprocate when it does happen.  And it will happen.  You just need to open your eyes and see it happen.

Here are examples of where opportunity can occur: Standing in line at the market, at a friend’s house, while holding the door at the local coffee shop, at a bookstore while browsing books, at work in the lunch room, out on a hike,  and while volunteering.  Everywhere and anywhere you can imagine.

But wait!  I don’t like to do any of those things.  I’m an introvert and I’m shy.  The issue here isn’t about not being able to see opportunity.  Many people can recognize the social cues of being friendly or flirty or being kind.  Those are relatively easy to spot for most people.  The real issue here is how to act on it.

Get out of your head and act.  Do.  Go and do.  Most people are scared in one form or another.  Most people are afraid of rejection.  My question to that is, “Is the possibility of making a new friend, or relationship, worth the possibility of getting rejected or even humiliated?”  All a person has to do is say one magic word.  “Hi.”  If it doesn’t work out, then it wasn’t meant to be.  If you are fearful, I recommend the book, “Feel the Fear and Do It Anyways” by Susan Jeffers.  It’s a good read on how to act when feeling fear.

I stumbled across this article on  Check it out HERE.

It’s a great perspective of how many men think women are out of their league.  It’s also an example of how men will stop themselves from acting on opportunity.

Someone usually has to step up to the plate, be confident, and make the interaction happen.  Typically, this is the man but at times, can be a woman.  “But wait!  I’m an introvert and I’m shy.”  To this response, I call phooey!  There are people who say that I can’t talk to people.  I can’t do this.  I can’t do that.  I don’t have this.  I don’t look like that.  And the excuses keep coming.  Phooey I say! Stop making excuses for yourself.

Here is the bottom line, when opportunity arises, which it will many many times, a person needs to be confident and step up to the plate to make something happen.  You know, confidence, that thing millions of women say is the sexiest thing about a man.  Confidence is not about being an extrovert, introvert, shy, loud, arrogant, obnoxious, having big muscles, owning lots of expensive toys, dressing in a specific manner.  Confidence is about being able to accept yourself, wholly.  Confidence is about being able to see your flaws and be okay with them.  Now how to become confident, that takes time and effort and I can take you there.

As I’ve said, the opportunities to meet good people and have great relationships are out there.  They are very recognizable and easy to see.  Opportunity is everywhere.  If you step up to the plate and take a swing, that’s another story.  It takes a confident person to take a swing and risk striking out.  When you make contact, and you will in time, you may hit a home run.  You never know what will happen unless you try.

Posted in Blog

The Good Ones are Taken

During a conversation with a client, he asked me where he could find people to date.  He says that he can’t find “any good ones.”  I chuckled.  I hear this question often.  My answer comes in two parts and the first answer is: everywhere.  You may find people to date everywhere and anywhere.  The second part is that you need to step up to the plate and say yes to opportunity when you realize the opportunity is there.

Really?  You can find a “good one” anywhere?  Yes.  If you are looking for a relationship, research has shown that many relationships start with an introduction from a friend or family member.  Parties and gatherings that friends and family have are a great place to meet people.  These people are generally good people because let’s face it; they are already friends with someone that you are close with.  Another place you can meet “a good one” would be at church if you are religious.  They have the same values as you and that would be a great base to start a relationship with.  If you enjoy volunteering, you can meet quality people while you volunteer.  Again, similar values to you.

Other places you can meet people would be in everyday life i.e. coffee shops, grocery stores and the gym.  You can also meet people through online dating, through meet up groups, and other groups that you actively participate in.  People are everywhere you look.  It’s not difficult to see that opportunity is staring you straight in the face if you learn to recognize it.  More on how to recognize opportunity in a future post.

This leads into the second point of stepping up to the plate and saying yes to the chance when you realize opportunity is present.  You never know what will happen when you open up your mouth and just say hello.  It could lead to the greatest relationship that you have ever had, the worst relationship, a friendship, a random conversation, a hello in response or maybe even nothing at all.  What do you really have to lose if you say hi?  The worst thing that can happen is someone doesn’t respond or is rude.  The best thing that can happen?  I’ll leave that one up to you.

The chance to find to find “a good one” is everywhere.  Recognize that opportunity and step up.

Posted in Blog

Conversations with an older adult: Treatment of Others

This is a new series of posts called, “Conversations with an older adult.” It’s pretty straightforward.  I enjoy sitting down with elders who have years of life experience and have conversations about dating, sex, relationships, divorce, family and life.  This topic is called “The Mother.”

While vacationing with my family, a member from our tour group comes up to me and tells me that he respects me and that my wife must be lucky.  I give him a look like, “What do you mean?”  Before I go any further, I’ll tell you a little bit about this man.  He appears to be in his 60’s and is Filipino.  He has been married for more than forty years, has three children and several grand-children.

The man senses my confusion and asks if I’m married.  I tell him my current dating situation.  He tells me that there is still plenty of time to find a woman to settle down with since I’m still very young.  I ask him why he said he respects me and that my wife must be lucky.  The Filipino man dropped some knowledge.

He tells me that it’s the way that I treat my mother.  He noticed that I respect my mother, do as I’m told and help her out when she needs it.  I’m not going to deny that.  I treat my mother with respect and am protective over her.  She’s getting older.  The elder continues saying “That the way a man treats his mother is the way that he’s going to treat his wife.  A mother is the closest woman in a man’s life until he meets his wife.  That’s why I said your wife is lucky!”

It’s food for thought.  It makes sense but, again, it doesn’t necessarily apply to everyone.  I’d say the biggest point to take away from my conversation with the elder is that when you are looking for a mate, think about the way they treat people surrounding them.  Every person counts- their family, their friends, your friends, the waiter at the restaurant that you are eating at and so on.  How do they treat people?  Is she respectful?  Does he yell at his mother?  Think about it.  How much different will your partner treat you if she treats her closest people this way?

Right?  Wrong?  When you are looking for a mate, do you look for this?  Let us know.  Share it on twitter and Facebook.  Like my Facebook page and follow me on Twitter.  Tell me what you think!

Posted in Blog

Ask The Date Boss: Young and Creeped Out

Dear Chris,

I’m a 21 year old woman.  When I go to bars, I get approached often.  Guys talk to me and buy me drinks.  I’m a little creeped out by these 30 year old guys though.  Seriously, I’m 21.  You’re 34.  What’s going on with them?  Why would someone in their early 30’s not be married? And still go after like young girls in their 20’s.  Do you think something is wrong with this guy? Or does he just wanna play?

-Young and Creeped Out

Dear Young and Creeped Out,

Thanks for the questions.  Your message brings up the old question, “Is age just a number?”  Yes and No.  First, Young and Creeped out, you need to read this article.  It discussed some general ideas about where people are in their life based on age.  It may or may not apply to you.

With that being said, there’s nothing wrong with someone not being married in their early 30’s.  Being married is a choice and not everyone wants to be married.  There is nothing wrong with being single.  There is nothing wrong with being in a relationship with no future of being married.  It’s a choice that each person will make.

As for a 30 year old man going after a young girl, again, there’s nothing wrong with that.  It’s a choice.  There are hundreds of preferences like short, fat, young, old, fit, brown eyes and etc.  Does he want to play?  Maybe.  Do they want something more?  Maybe.  The only way to know for sure is to talk to him and find out.

My hunch is that he wants to play.  There’s nothing wrong with that.  Have a drink with him.  Have a conversation with him.  You are both grown adults and can make grown up decisions.  If you want to play, then play.  If you aren’t interested, just let him know.  Don’t be the person that leads the other on.


If you have any questions that you want to ask, shoot me an email, hit me on Facebook, comment below or on twitter @TheDateBoss.

Posted in Blog