PSA: First Date Conversation

As a relationship expert, I do a lot of coaching. I constantly hear he/she did not bother to ask anything (on a date) about me, except my age, marital history, and income.

A first date can be uncomfortable, especially if you arrive with a bad attitude or don’t even attempt to give the other person a chance. However, if you can walk into a first date with a great attitude and no expectations, things will go much smoother… this is actually true with everything in life!

During a first date, both people are supposed to use this time to get to know one another a little better. The keyword here is …BOTH… but at least seventy percent of the time this doesn’t happen.

We’ve all been on that date when one person is so self-absorbed that they spend the entire time talking about themselves, what they have, where they have been, or who they know. (This is a RED flag)

FYI: If a first date conversation includes: Can you show me photos of your ex’s? How much money do you make? How big is your house? How many cars do you have?… RUN! Don’t waste your time lecturing an adult with poor priorities, just leave.

So, today I want to set the record straight with a few extremely basic guidelines:

  1. Remember, a first date is also the first impression, and first dates are inherently awkward. Which means the first impression may not be so great, either. As long as the person seems nice enough, you share some basic interests, and there is some chemistry, try for date number two. On your second date, things are generally way more comfortable and you can really get a better idea of who someone is.
  2. Always go with your gut. If you go out on a first date and leave with the feeling that something is just not right (i.e your instincts are warning you, not a superficial judgment), then maybe just move on to someone that doesn’t make you uncomfortable to be around. Don’t waste time here…
  3. Ask questions, appropriate questions, and lots of them! Ask about interests, life goals, family, pets, favorite foods, or television shows. Ask about holidays, culture, and even if they enjoy their career. Don’t talk about break-ups, divorces, finances, how you want a baby by date three, or anything else that you would not disclose to a total stranger. Use this time to get to know someone and allow them to get to know you. This is NOT an interview and should be fun and relaxing.
  4. Lastly, please stop with the games. There is no winner when this happens. Grow up. If you don’t want a second date, say it. If you like someone, tell them. If you want a second date, ask right away. Don’t wait around because you don’t want to seem too excited or desperate. Pick up the damn phone and call.

“The early bird gets the amazing relationship!”

I Don’t Want to Make my Parent’s Mistake

Reader’s Question:

I’m a senior in high school. I am considering if I should start college next year or not. Both my parents want me to go to college. My problem is that I really don’t like school. Both of my parents went to college and it didn’t do much for them. They both still work long weeks and we are not broke, but things still get tight. If college didn’t help to improve their finances, then what’s the point of wasting all that time and money for nothing? College is very expensive. I work to make money and I don’t think I need college to do what I want in life. I’d like to be a chef and own a few restaurants one day and for that, I need experience, not education, correct? How can I help my parents to understand that I don’t want to make their mistake?

Incorrect! You need both.

I wish you were the neighbor’s kid so I could hunt you down and give you a good talking!

Please, try not to be offended… you truly have no idea what you’re talking about. That is okay though, the next stage in your life will be a lot of lessons and learning.


Lucky for you, you already know what you want to go to college for and culinary school’s exist!

If you want to be a chef and own a restaurant, you need to attend culinary school. You should also have spoken to a career or college counselor about this, as you clearly did not know culinary school’s offer 4-year degrees. Culinary school degree programs cover basic professional writing and business skills, which are needed to be successful in your extremely competitive industry.  Running a business is not all common sense, you must learn first. Or, you will fail!

You must learn from the best. You must surround yourself with those much more experienced than you. Why make a mistake someone else has already learned from? You want to do things the smart way? Learn from others and trust their experience.

You need college. How do you plan to be a chef and own your own restaurant if you don’t know squat about running a business or cooking at a high level? Are you going to work your way up from washing dishes at a fancy restaurant with the hopes that they let you peel carrots after a year? Does that sound better than going to college?

Also, if you think your parents work long weeks as professionals, wait until you work all hours of the night as a cook… all weekend long, and on holidays.

Do you think a bank is going to give a cook that makes $12/hr with no education or financial leverage a loan for that restaurant? How will you manage the front of the house if you’ve ever only known the line? Who will handle your payroll, taxes, vendor invoices, budgets, and sales forecasts? You won’t be qualified to do so with no college degree or administrative experience?

Lastly, your parents did not make a mistake by going to college. College is never a mistake. You show your age by making such comments. Most middle-class families (with a college education) still have a hard time financially. You have no clue how much harder life would be without both parents having higher education. If your parents had no degrees and worked restaurant jobs, waiting tables to get by, you would be in the first college class that let you in!

College does not guarantee success, true. Success is up to the individual. Did you know a college degree usually means you will make at least one million dollars more throughout life?… that makes it worth the $50k (or higher) price tag.

Be grateful your parents are pushing you to better yourself, not many kids have that support at home these days.

Knowledge is power… and you will need every bit of power to make a nice life for yourself.

Start looking into culinary schools that offer 4-year degrees and thank your parents for supporting your future at a higher education organization. They want what’s best for you and that’s not slinging burgers for the rest of your life.

Am I a Bad Mom?

Reader’s Question:

 My best friend and I are both pregnant! She has two other children and this will be my second. She is a natural mother and loves being pregnant. She never complains and I have never heard her raise her voice to either her children or her husband. She’s perfect. I scream and yell, cry and complain. I hate being pregnant and while I don’t mind the kids, I do count the days until they will be able to wipe their own butt. I’m tired and just so done with it all and she wakes up each day ready to take it head-on, with neat, well-behaved children attached to the hip. Why can’t I feel more like her? Am I a bad mom for wishing their time with me away?

I laughed as I read this for the second and third time. You are not alone. There are many women who experience the same feelings about pregnancy and parenting as you.

I have two children and I can honestly say that I hated almost every moment that I was pregnant. I cannot remember a moment in either pregnancy where I thought, WOW I AM FREAKING LOVING THIS!

Most women I talk to feel that same way. Pregnancy is not for everyone. It’s fine to not love it, but try to stay positive as it will be over soon and you can choose to never do it again.

Every parent I know is, or has been waiting for the day their children leave home to venture out on their own. Raising children is hard work and takes immense efforts. It’s hard for you. It’s hard for your husband. It’s hard for the children. It’s hard on your marriage.

It’s hard… so any reasonable person, from time to time… will daydream. I do this multiple times a day. Shoot, I took a break writing this just to daydream a bit! Imagine the day you finally get to do anything you want! The day with no chance of butt wiping, teething, soccer games, concerts, school lines, sick days, snow days, bad grades, periods, cell phones, social media, bullying… it’s endless.

The point is, what you feel is normal. Even when things are going “great” and seem “easy” and you still feel like you want them gone, that’s normal too! Being a parent is hard work and we struggle every single day.

Just breathe, this time will be over before you know it (ish).

How Do I Talk to My Wife About Our Sex?

Reader’s Question:

I’ve been married for about five years. We have two children and all is, mostly, well. My wife and I are not having enough sex and more troubling is that we don’t really talk about sex, ever.  We never talk about what we like or how we want things. We never discuss why we don’t have sex, even though its often a hot topic to start an argument. This is not about our children and the toll they can take, we know this. This is about us and how we communicate physically with one another. While we’ve never talk about sex, our sexual activity has taken a serious decline this year. It makes me wonder. Is it normal I don’t know about her sexual past and her mine?  Is it normal I don’t know her favorite position or even if I get her “there” ever? I can obviously bring this up with my wife, but I’d like some tips on how to keep bringing it up and keep the conversation out in the open. 

Great question! Yes, this is all very “normal,” but you both owe each other more.

It is common that couples don’t discuss their sexual past and it’s not like she is purposely hiding it from you. Why discuss? Do you think she is lying about something? Do you want juicy details of every man she has taken to bed? I can assure you no wife wants to hear this about her husband. The past is the past, so why allow it into the present? Who cares?!

Is the point to judge your wife based on her past? Think about why you want to know.

Dry spells in a marriage tend to make minds wander. Have faith that your partner told you anything that truly matters and leave the rest alone.

I’ve talked with hundreds of couples over the years with this same issue revolving around intimate communication. It can really hurt the physical side of your marriage, so you should speak up sooner rather than later, and so should your wife.

Make things easier and go first.

I know you say it has nothing to do with the kids, but please keep in mind that children of all ages take their toll on a marriage. Think what you like, but someday you will look back and probably realize that the children are a big issue here. I’ve been there and wish I’d have known that things would be even worse than I imagined (emotionally).

Kids are hard. Have you ever asked your wife if they children have anything to do with your lack of sex?

Maybe it’s easier for you than her right now. Two children in five years would take a toll on the best of us, so giving this perspective some deeper thought is a big recommendation. Remember, it can be hard for some parents to admit their kid is the cause of something negative

The problem with not talking about sex in your marriage is that it creates a crack in the foundation. It’s human nature to think about sex and so it must be on both your minds from time to time. The fact that you two are uncomfortable talking to each other about your intimacy should stop. Why do you think you cannot communicate your desires to your wife? Does it make you uncomfortable? Are you nervous she won’t want the same things? This is a great place to start. Why is the communication on this topic different than any other in your marriage? Figuring this out will help you to move forward.

Sex is very important to a marriage.

You’re on the right track. You know there is a problem and you are making efforts to fix it. Keep the conversation light and use “I statements.” Don’t place blame for the lack of sex or communication, just voice your concerns and your plans to break this cycle. It will be frustrating, but well worth the effort. Bringing this conversation to the table now can save your marriage a lot of sexless, sleepless nights. Just be forward and honest.

Explain to your wife that you want more sex and you’d like to discuss sexual preferences… because you want her happy and pleased. You will never be able to get her “there” if you don’t know what she likes and the same goes for her.

You are married and open to sexual exploration within your marriage! You want more sexually and that is okay. Starting this will be hard. This can bring anxiety or excitement or both, so try to be understanding.

In marriage, it is important to grow together, even when things aren’t peachy.

My Teenager is Financially Oblivious

Readers Question:

 I have a teenager who is now driving. Some parents are giving their kids new cars and a full-ride during high school. Meaning… spending money, date money, gas, car insurance, sports, cell phones, et cetera… I think this is preposterous. What are they going to learn from this? Many young people today come with a huge sense of entitlement. They will not learn how to be responsible in college if they go in with blinders on. We can easily afford our sons habits, but my husband and I do not agree on this issue. I want him to grow up and learn some financial responsibility and my husband thinks he should enjoy this time being a kid. I know you have a teenager. What do you make him pay for monthly? Any advice for us on this hot topic?

I feel your pain here. This is a tricky topic to cover and I don’t think there is anyone answer that works. Every kid is different and every family’s financial status is different, so what works well for one could be impossible for another.

I one hundred percent agree that kids today have major entitlement issues, which are generally learned behaviors, so you are absolutely right to want to stop and take some time to review your parenting policies.

Just like we try to hold our children accountable, we must hold ourselves accountable as well.

I am guessing your kid is 16-17 years old, therefore he is no longer a kid! He is a young adult. He needs to learn valuable life lessons now, while they won’t ruin or negatively affect his life moving forward. The sooner this perspective is shared by your husband, the better.

College is only 2-3 years away at this point. Your son needs to know how to “adult up” (I don’t use “man up” because young ladies are included here) and take care of himself in every aspect of life. He will probably just expect you and Dad to take care of things otherwise. And seriously, what parent wants that? A large part of being a good parent is enabling kids to be competent and responsible humans. We owe this to society and it means they will most likely never move back into your house when they are older! Everyone wins.

During high school, parents are generally focused on grades and teens on their social life. It is important for parents to be realistic when settling ground rules for financial responsibilities in high school. A lot of these ground rules should be determined by your teen’s needs. i.e. what areas does his character need improvement? Is he taking advantage of certain things? Is he too busy with school or sports to work part-time? Can he do chores around the house to earn spending money?

We aren’t making them pay for their life because of a tight budget, we are making them pay for their life because they should be familiar with some of the hardships and tough decisions they will encounter very soon and very often. We are working on mental preparation and competence.

If parents can give their teens a taste of real life here and there, it will give young adults the confidence to tackle their own issues as they grow. They will be confident when encountering problems and handle them… or they will be scared and ignore them.

You have to sit down with your husband and decide together what you think is fair and realistic for your family.

 Maybe start by reviewing the cost of your teen’s current privileges. Add up a month of cell phone, insurance, gas, et cetera. Take that to your husband first. Decide on what a fair percentage is for your son to cover. Discuss if he should get a job or can earn money at home. Then take that information/decision to your son and lay it all out.

I Will be Alone for the Rest of My Life

Reader’s Question:

 I am not an attractive man and it doesn’t help that I am short (5’3”) with a below average penis. I was in my late twenties before I finally had my first date and at thirty-five, I am still a virgin, as a refuse to sleep with escorts. I am not suicidal or depressed, but I would like to figure out how to accept my situation and move on. How do I accept that I will be alone for the rest of my life?

First, you don’t have to be alone for the rest of your life, unless that is what you truly want. Believe it or not, there are people out there who will love you for the true you.

You are not your body. You are not your looks.

 I’m proud of you for taking a hard look in the mirror and accepting the truth of how difficult romantic relationships are for you. That is not easy! It seems that a lot of what hinders you are factors that are out of your control.

You have allowed yourself to move on with what you have and who you are physically. Now, it is time to decide what you want from life.

You don’t want to be alone! You need to stop saving yourself from possible disappointment or rejection.

If you decide to accept being alone for the rest of your life, you’re simply giving up. You need to find your self-worth and confidence in who you truly are. Love yourself enough to move past this. You are just wrong if you think love is out of your reach because of your physical makeup. Just like people that think aliens aren’t real…we can’t prove it yet, but the numbers say the probability is virtually guaranteed. I think your chances of finding a happy, rewarding relationship are virtually guaranteed too, but you must be realistic, honest, positive, and confident.

 I understand saying “be confident” is much easier than actually doing it, but fake it until you make it. If you stop portraying your body as who you are, potential lady suitors will follow your lead.

She is out there. Maybe she is an inch shorter or wider, maybe she loves coffee and you despise it, maybe she is blonde and you only wanted to love a brunette… I do not know. The point is, your way of thinking is part of the problem.

YOU DESERVE LOVE just like everyone else and there is a someone special out there meant just for you, you should make an enormous effort to find her.

Finding love isn’t easy, but you still have to try.

You have to put yourself out there knowing you could get hurt time and time again… until eventually, you don’t. This is just how it works.

Work on your appearance. Stay in shape. Maybe, if finances allow, invest in an image consultant who can help with your overall style. Don’t wear platforms in your shoes or doing anything misleading or extreme.


When it comes to the bedroom, make use of toys and everything else on your body. Become a damn “spider monkey” in bed. Learn things she has never heard of and surprise the hell out of her. She will remember your penis is smaller than she would like perhaps, sure. She will also remember the crazy, freaky, new, exciting sexual experience you gave her that no one else ever has. Satisfying your lover in the bedroom doesn’t solely rely on penis size, never has. Some women can’t climax from intercourse alone in the first place.

For now, get your attitude right and think only confident thoughts. Never consider quitting or being alone. Focus only on presenting your best self.

Chin up! You have work to do!

P.S. I never do this on JAM, but I suggest using my workbook to help you analyze who may be a great match for you. Here is a link to the workbook. Click Here


Top Ten Reasons People End Relationships

  1. They don’t feel appreciated
  2. Infidelity
  3. Financial incompatibility
  4. Lack of communication
  5. Lack of effort
  6. Major life event
  7. Boredom
  8. Lack of met expectation
  9. As you grow, you do it separately, therefore growing apart
  10. There was no real foundation in the first place