Learn The Ups & Downs Of Dating Someone With Kids

dating someone with kids header

In this day and age, dating someone with kids is not that uncommon.  We all want to find our perfect match and sometimes that means our perfect match had a life, spouse, and children before meeting us.  Many times when clients hire me as a dating coach they have doubts and anxieties about getting involved with someone with kids (even if they have kids of their own!).  This blog post will lay out some of the most common areas I address with clients on this subject.

Single parent dating a non-parent

dating someone with kids - single parentYour free, flexible, mobile and loving life.  That’s how many adult professionals who don’t have kids are seen by single parents.  As a non-parent, it’s true that you likely don’t have certain demands on your time.  Other than work and commitments you choose to dedicate your time to, your time is likely your own.  Now if you have a caregiver role or something else that’s a major responsibility in your life, then you understand

Questions to ask when dating someone with kids

questions to ask Communication is key in any relationship, but especially when there are other major factors that will impact that relationship.  In this case, I’m talking about the time commitment of the partner who has kids.  When I’m hired as a dating coach, one thing my clients come to understand is the need to get important questions answered early.  Some of those questions include:

  • Who is the custodial parent?
  • What is the relationship dynamic with the other parent?
  • How does your child (or children) feel about you dating?
  • Are you looking for a serious or casual relationship at this point?
  • Do you have open and honest lines of communication between you and your child (or children)?
  • How do you plan to effectively manage spending quality time with me when you have important childcare responsibilities?

adorable kidsThese questions may seem forward but guess what, asking them early on in dating will allow you to make a better decision about whether to continue dating the person with kids or not.  Truth is most single or parents who share custody really don’t think about these things.

Asking these questions will allow them to better understand where you’re coming from and what the expectations are.  Face the reality that the welfare of the children will come first.  This means a very real possibility of missed dates due to events/illnesses/surprises that may arise with the kids.  If this is something that you’re not ready for, then dating someone with kids is probably not for you.

Being in a relationship with a woman who has a child

dating someone with kids - the womanThere is no “one size fits all” answer to this question, especially since in the scenario where a person is dating someone with kids, they will likely be a bit more impacted if the woman is the one who has a child or children.  The reason for this is simple. In my experience as a professional life coach, I’ve noticed that women are usually the primary caregiver in single-parent scenarios.  If you are a person who likes a woman who has the responsibilities of a child or children, be prepared to have certain limits on time and location for dating.  What I mean is there will be times when she is simply not available.  Especially if she is the custodial parent.  Also, recognize there will probably need to be extensive planning for any quick getaways or romantic vacations.  She likely just can’t leave work on Friday and catch a flight somewhere with you.  She has responsibilities that are far more important than you and that’s something you need to understand upfront.

Often when clients are trying to find a life coach, they want a person who agrees with what they say.  That’s why professional life coaches have Discovery Sessions.  The purpose is to clearly lay out what a life coach does as well as ensure the potential client understands that questions will be asked that might challenge their way of thinking.  This means if you believe when you’re dating someone with kids that their priorities need to shift, a professional life coach will dig deeper into this area to see what you actually want.

  • What is the end result that you’re actually seeking in the relationship?
  • What makes you think that a woman with children should shift her priorities?
  • How would you feel if those were your kids and your ex was dating and decided to shift her priorities to someone she was dating?

As a professional life coach, I ask that you put the shoe on the other foot and broaden your perspective.

When to introduce kids to boyfriend

introduce kids to boyfriendIf you’re the non-parent in the scenario of dating someone with kids, and the relationship is going very well over several months (at least), you’re going to be faced with meeting the child or children of your sweetie.  While dating someone with kids can be awesome, this is something that many of my clients have come to me with tons of anxiety!  If the relationship has been going well, you should have a fairly clear idea about some of the following characteristics of your girlfriend’s kid or kids:

  • ages
  • personalities
  • temperaments
  • extracurricular activities
  • any (major) health issues
  • relationship with their other parent
  • how they feel about their mom dating

With these key facts in mind, you can have a very open and honest conversation about when and where to meet her kids for the first time.  For example, if she has younger children, an amusement park or a ball game where you, your girlfriend and her kids all go out together might be fitting.  If she has a teenager who likes a certain genre of music or has a specific hobby, something music-related or geared to their hobby that you, your girlfriend and her child can all do together may work.

meeting the kids for 1st timeWhatever you chose, in my experience as a professional life coach, neutral territory is usually the best.  Come in separate cars and leave in separate cars from a location that is not their home with their mom.  This isn’t an absolute rule but what I’ve seen is this approach gives the kids some space and comfort as well.  After whatever activity you all decided to do together, the kid or kids can talk to their mom on the ride home about their thoughts about you.  On the same token, whether the ‘meet and greet’ went good or bad, you riding home in your own car gives you time to process as well before the next time you talk to your girlfriend.  Some feelings you want to be very aware of include:

  • How do you feel about her kid or kids overall?
  • What was the kid(s) energy and attitude towards you?
  • What was your energy and attitude toward the kid(s)?
  • Are there any dynamics between mother and child(ren) that stood out to you?
  • Would you want to have another outing with your girlfriend and her child(ren)?

Be honest here.  The answers to these questions will clearly determine if there is a future in dating this woman.

Is dating a man with a child worth it

dating someone with kids - manSimilar to dating a woman who has kids, there is no “one size fits all” answer to this question.  When clients contact me to hire a dating coach, their situations can run the gambit of the guy sounds like he is totally worth it to dump his ass yesterday!  But seriously, the dynamics of the man and his child (or children) are very important when it comes to the right choice for you.  You also must consider how big or small of a role you want to play in the lives of the children if the relationship gets serious.  Dating someone with kids is hard but only you can weigh the pros and cons of your particular situation.

For example, if the man that you’re dating seems to be a very attentive father with appropriate boundaries with his ex and you have a positive rapport with the kid(s), then this seems like it would be a relationship that’s worth your time and energy to see where it goes.  On the other hand, if you’re dating a great guy who has an ex who causes drama and/or kid(s) with whom you don’t have a good vibe, you may want to really think hard about the personal cost of continuing in the relationship.

dating a man with kidsThis may sound harsh but the reality is the guy you’re dating decided to marry and have kids or just have kids with the person he did.  If he calls her “crazy”, that’s a cop-out.  She is the same person she has always been, he’s just now willingly seeing the characteristics of her personality that the people around him were probably trying to tell him about far before he had kids with her.  So if she’s “crazy” and the kids are a mess, that’s his problem, not yours.  Save your time, heart and sanity and get out of any situation like this asap!

Tips for dating someone with kids

I want to recap some of the major takeaways that you need to keep in mind if you decide that dating someone with kids is for you:

  • Ask critical questions upfront when dating someone with kids
  • Meet the person you are dating’s kids for the first time in neutral territory
  • Drive your own car when meeting the person your dating’s kids for the first time
  • Be honest about your own level of comfort and flexibility in this type of dating situation
  • Understand the cost of staying in a relationship when dating someone with kids who has drama with their ex or their kids
  • Limitations on time, availability, and mobility come into play when you’re dating someone with kids — spontaneity is usually not an option at all or very limited


tips for dating someone with kidsDating someone with kids can be fabulous or it can be a total waste of time.  It all depends on the attitude you go into the relationship with as well as the person (and their situation) you’re dating.  Either way, you need to be very honest with yourself before even considering getting involved in this type of dating.  Parents have responsibilities and obligations that, if you’re a non-parent, you may not understand.

If you meet a fabulous man or woman and you two have a great connection, and they tell you they have kids, understand what that means in terms of them having romantic relationships.  Know what you’re getting into and know that it’s ok if it’s not for you.

Are you currently dating someone with kids?  Are you struggling with your feelings in such a relationship but know that this person is for you?  Interested in learning more about how to approach and date in this type of situation?  Then book a session today!

Schedule Appointment

Other blog posts of interest:

Are You A Hot Mess At Dating?!
Importance of Sex in A Relationship
How To Be Successful After A Break-up
Cool Posts – Volume 1 (Dating After Divorce)
Bold First Date Questions That NEED To Be Asked

Are You A Hot Mess At Dating?!

Are You Just A Hot Mess to Date?Are you bad at dating?

Are past relationships similar to something off of a reality show?

Just bad at love?

If the answer is “yes” to any of these questions, read on!

We all want successful relationships. In every area of our lives, we want positive familial, platonic, work, and romantic relationships. Stress and strife need not apply.

Well, if you don’t currently have peace and success in your romantic relationships then you have to start with a good look in the mirror.

In this post, I will give you a behind-the-scenes look at some of the tough questions I ask clients who decide to hire a dating coach.  Answer these questions and you’ll soon discover why you are indeed bad at dating.

Question #1: How do you define intimacy in relationships?

Take a few minutes to define what intimacy in relationships looks like. Write it down. Be clear and honest with yourself about your definition of intimacy.

Are you a touchy feely person and you want the same in a partner?

Write it down.

Are you more comfortable with long distance relationships?

Write it down.

Is a mental connection more important than a physical one?

Write it down!

Whatever you want in terms of intimacy in relationships, you need to be clear about it, for both yourself and your partner.

Question #2: What lessons have you learned from your past romantic relationships?

I know I’m ripping the band-aid off with this question.  Reflecting on past relationships can be painful.  With that being said take a moment to look at the things you have learned from those past relationships.

The good, the bad, and the ugly.bad at love hot mess to date pic

Whether you experience joy or pain at the memory of those past relationships, the fact is that you learned something.  What are some of those “I will never again [fill in the blank]” and “I will always [fill in the blank]” statements you hold in your heart when you think about those relationships.  These hard-won nuggets of wisdom are important for your future success.

If you are having trouble defining those lessons because you think dating is impossible, know that when you hire a dating coach you will not have to go through this process alone.  The partnership will allow you to recognize signs you are bad at dating as well as increase self-awareness.

Question #3: What do you want out of your next romantic relationship?

Honey, life isn’t a movie and fairy tales are for children. It’s time to be honest with yourself about the value you want to get out of your romantic relationships.  Yes, you should dream big but please remember life is not a rom com.

Life isn't a movie and fairy tales are for children. It's time to be honest with yourself about the value you want to get out of your romantic relationships. Click To Tweet

Do you want friendship and support? Then you need to define what that looks like for you. Do you want the relationship to teach you something about love and intimacy? Do you want the relationship to be totally within your current comfort zone and pattern? Do you want the relationship to be a total change from what you have experienced before in relationships?  At times, dating is impossible but truthfulness will allow you to navigate the murky waters of dating.

Question #4: What do you have to bring to the table in your next romantic relationship?

The basis of this question is for you to become what you want to attract. Take a look at what makes you great at being you. Being able to identify the perks, quirks, and advantages to your personality is very useful. Now consider all of the things you’ve just identified about yourself in the context of bringing something positive to your romantic relationships.  Honestly, this is the questions that many clients get stuck on so do feel bad if you do too!  Also, don’t feel as if you have to go it alone.  Hire a dating coach to help you identify and refine those fabulous parts of what you bring to a relationship.  You may be bad at dating from a simple lack of awareness in what you choose to share at the table with an intimate partner.

Keep it simple and make a list. Now that you have figured you out a little, are there any areas where you want to be able to bring more to a relationship (i.e. money, emotional support, etc.)? If you have identified any opportunities within yourself upon self-reflection, then write those down as well.  Start thinking about ways to improve.

Pic of not being a hot mess to dateQualify for Higher Paying Jobs

For example, if you want to be able to bring more money to your next relationship, start looking for a higher paying job. Or start looking at the type of training and/or education you will need in order to be more qualified for higher paying jobs. Some books that I recommend on this topic include:

Improve Emotional Intelligence

Another example of identifying opportunities for what you have to bring to the table in a romantic relationship might include being more of an emotional support to your partner. Well, to be able to be more of an emotional support (to anyone) you have to develop a higher level of emotional intelligence.
You may be asking yourself “what is emotional intelligence?!”
Some books that I recommend on this topic include:

Question #5: What advice about relationships would you give your best friend?

We all can give great advice when we are on the outside looking in. Take the time to think about what relationship advice you would give your best friend. What would you bring to their attention? What habits about your bestie would you share? For example, if your best friend always seems to date the type of person who they think they can “save” from themselves then bring that up! You know that man or woman that is a total trainwreck but your friend always wants to see the best in that person.


As a quick recap, understand the five (5) questions that will help you understand why you may be terrible at dating are:

  • #1: How do you define intimacy in relationships?
  • #2: What lessons have you learned from your past romantic relationships?
  • #3: What do you want out of your next romantic relationship?
  • #4: What do you have to bring to the table in your next romantic relationship?
  • #5: What advice about relationships would you give your best friend?

Are you being honest with yourself about how easy or difficult it is to date you?  Read through this post again.  Answer the questions truthfully.  Understand that being bad at dating is a choice.  Whatever answers you don’t like, start making plans to address those areas of your life today and partner with a dating coach to achieve ultimate success.

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Like, comment, share and subscribe!

Other posts that may be of interest:

Dating After 30
Importance of Sex in A Relationship
Bold First Date Questions That NEED To Be Asked
Overcoming Self-Sabotage: 3 Steps to Take Today
7 Signs That Intimate Relationships Aren’t Your Cup Of Tea

Bold First Date Questions That NEED To Be Asked

bold first date questions

First dates. We’ve all gone on a few.  They can be something out of a romantic comedy or something out of a cheesy horror film.  One thing I’ve learned from working with coaching clients is that many times deception and lies start from the very first date!

Here are some deep first date questions that absolutely must be asked.  By asking these (sometimes uncomfortable) questions, you will avoid stress and drama in any budding intimate relationship.  Also if you don’t feel quite ready to ask these possibly awkward first date questions, you will see the value in deciding to hire a dating coach.

Asking first date questions that are a bit bold will save you time, energy, and possible heartache later! Click To Tweet

First Date Question #1: Ask about other current relationships

first date questions relationshipsFirst things first.  Any person going out with someone new for the first time probably has limited knowledge.  Especially of that person’s relationship history.  Here are some deep first date questions that should be asked to ensure full disclosure.  Ask if the person is:

  • married,
  • engaged,
  • dating (casually or serious),
  • in  a “friends with benefits” situation,
  • has a crazy ex,
  • shares parental responsibilities with someone else

I have countless clients who have ended up with broken hearts because they assumed the person they were dating was single.

Don’t assume!  Ask point blank.

I have found that’s it’s much harder for most people to lie directly to someone’s face.  This means “players” will be found out quickly.   A lot of heartache and time will be saved by understanding the other person’s relationship status upfront.

First Date Question #2: Ask about sexual orientation

first date questions- sexual orientationToday people are more open, honest, exploratory and fluid in their sexuality.  This means that it’s very important to know the sexual orientation of a potential intimate partner.  When I coach on this with clients, they are skeptical of asking awkward first date questions such as this.  This means my goal when a client decides to hire a dating coach is to ensure that they understand the “why” behind the question.

I tell them that the goal of this question is to ensure total comfort and acceptance of the sexual orientation of the person they’re dating.  If this bold question is asked on the first date, it will avoid any surprises in the future.

First Date Question #3: Ask about thoughts on exclusivity in intimate relationships

This is an optional first date question.  Some people aren’t concerned about monogamy in their intimate relationships.  If that is the case with you, then skip this question.  However, for my clients who do want exclusivity and monogamy in their intimate relationships, this is something that should be discussed on the first date.  The more informed a person is upfront, the better decisions they can make.

I know, I know, these questions may seem a little silly, blunt or scary to ask on the first date.  However, they don’t need to be asked like a person doing a job interview!  Each of these questions can easily be added into casual dating conversation without digging too deeply.


Dating is hard enough.  Asking the right first date question can:

  • prevent misunderstands
  • address false expectations
  • help you to better understand the person you’re pursuing an intimate relationship with

and most importantly…save you a TON of time, energy, and emotion.  Anyone who wants to build their confidence and comfort with asking such questions would greatly benefit from the decision to hire a dating coach.  Don’t put love on hold any longer, book today!

Schedule Appointment

Like, comment, share and subscribe!

Other blog posts of interest:

How Are You Finding Your Bliss?
Importance of Sex in A Relationship
7 Reasons Women Are NOT Calling You Back (For Men Only)
7 Signs That Intimate Relationships Aren’t Your Cup Of Tea
Dating Around: Controversial Reasons Why He is NOT Calling You Back! (For Women Only)