Question #6

How to make time for hard conversations?

He Said: (response by Patrick G., Circumspect Life)

If there is not a single hour or two in any given week with BOTH people are free, then THAT is the time when both people need to have such conversations.  If such a scenario doesn't exist, then something is awry.  Making time is just that, putting something ELSE off to have a talk.  A woman who doesn't have the time, interest, or ability to do this - is not suitable for me. Next.

She Said: (response by Erica H., Vine Life Coaching)

First, it takes courage to have hard conversations. If you can become clear about the issue, how you feel, and what happened for you to feel the need to have a hard conversation. Secondly, analyze the roles of each party in the situation. Were you responsible for anything and if so what? Were they responsible for anything and if so what? Keep in mind not to attack the person, but rather ask them questions with an objective mindset. Lastly, here are so example questions to ask and responses, “Do you remember when this happened?” “What do you remember about it?” “I want to share with you how I feel and what I remember.”

When you are fully ready to have this conversation under the right private circumstances ask them if you two can talk or set some time to talk. If they care about you, they will be willing to set some time with you to talk. If they do not want to have a conversation, you will have to evaluate how you can process your feelings on your own. Or how can you move forward even if they do not want to have this conversation.

Pray, ask God to give you the strength, and courage to have this conversation. Ask God to prepare your mind and heart and the other person. I am sure as God sees your heart, He will prepare you to let your feelings be heard in this hard conversation. 

Question #7:

What’s your advice for young women dating today?

He Said: (response by Patrick G., Circumpect Life)

Be the best version of yourself you can possibly be in EVERY aspect of your being.  Only associate with men (friends or otherwise) who are doing the same.  Find yourself in places where such men frequent.  You'll know this by OBSERVATION and not merely through conversation.

Ask this question: "is this man someone whose word I can trust, who I would go to for LIVING advice, and someone I would have no issues FOLLOWING?"   Look for a man who you could honestly say, "he has his head on straighter than I do".  Keep him.

She Said: (response by Jenise L., Over the Hump Messages)

This answer depends on the level of experience the woman has...the main thing is to know what your intentions are for dating. For sport or purpose?

If you’re dating for sport...set boundaries around frequency (how often you spend time together) & whether or not you will be physical. Set those expectations up front so you’re both clear on what the nature of your relationship will be.

Dating for purpose is very selective & intentional. We all make “The List”...however be sure the list is not based on a fairytale but faith. Know and understand how you desire to be loved (what are your love languages). Be in the moment & be observant. Know what your deal breakers are and what you desire for growth.

Most importantly be confident in your singleness. Understand what makes you happy while single and that will give you clarity while dating. 

Question #8

How to be honest without hurting feelings?

Question #9

Why is it hard for a man to communicate his heart’s desires?

Question #10

How do I tell him/her you don’t give 100% to the agreed upon goal we set?

He Said: (response by Cory Cabri, Living Life on Purpose Podcast)

It's not a realistic way to be honest without hurting feelings because you can't control how a person is going to react to your honesty. What I would suggest is consider how the information is going to be fruitful to both you and the other party. How will your honesty benefit the two of you? If it's only going to get something off your chest, then it's likely going to hurt the other person. I would advise against that approach. I know there are times when you may need to get something off your chest. I would suggest considering the time in which you want to share the information in that case. If you are in an argument or heated discussion, you're likely going to say it in a tone that comes off judgmental. What is the right time? The right time is when the two of you are in a peaceful setting. In that setting, you can offer your honesty in a manner that will be humorous or in the form of a question? All in all, seek to be fruitful with your words and not merely truthful alone. 

She Said: (response by Jenise L., Over the Hump Messages)

If you’re in a relationship then you know how they feel about certain things...keep that in mind but also recognize that it maybe uncomfortable but it doesn’t have to be harsh. Be honest but considerate. Don’t offer a solution unless solicited...sometimes all that’s need is awareness...but do be encouraging.

He Said: (response by Cory Cabri, Living Life on Purpose Podcast)

It honestly depends on the man in regards to how they want to share. Some men feel it takes away their masculinity if they share their hearts desires. You have men that are running game and they're not going to share that their true heart's desire is the bed because they don't want to scare you away. There are also guys out there that may take longer to gain trust from you. In those cases, you have to be patient and open to get him to open up to you if you feel the person is worth your time. Lastly, men like women, reserve certain people for sharing their heart. In this case, you may never become the person he truly feels comfortable with sharing his hearts desires, goals, or ambitions with. You as a woman or man will have to determine if you're comfortable being in that situation if you're not married. If you are married, you'll have to be patient and constantly show them that you're there for them. You'll have to let them open up to you when they're comfortable because you'll push them away otherwise. 

He Said: (response by Patrick G., Circumspect Life)

It's not hard.  They don't trust you yet.  And may not do so for a while.  This is NOT a red flag.  This is how a man on his square does, and should, roll.   That does NOT mean he's going to (or should) side-eye you every time you open your mouth or make an inquiry.  He should be compassionate and attentive, but not a blabbermouth.

When he trusts you, he'll tell you (almost) anything, unless he has issues with intimacy.  You'll know this long before you start having conversations about their hearts' desire.  He should be open to sharing basic things about himself early on...his goals, his vision, his mission, his faith, basic things about his background and family of origin.  Anything beyond that is not appropriate unless your association falls under what I mentioned in Question number 3 - exclusivity.

A man who wears his heart on his sleeve and tells you everything after the first couple of times of meeting you is not a properly comported male...he's more like a chatty indiscreet female.  Run from this dude.  He'll fold under questioning and is not a reliable partner in crime.  

He Said: (response by Patrick G., Circumspect Life)

I'd say you should have those goals written down and review them periodically.  If you're both holding each other accountable regularly for a particular goal then you mitigate the need to have many conversations about who is not pulling their weight.  If the person has a pattern of avoiding accountability, then that is a red flag.  You certainly want to find these things about early on in the exclusive phase, because taking such things into Marriage is a major no-no.  Reliability and accountability are character issues.  Someone with poor character is not a good partner for a believer, especially.

She Said: (response by D. Michelle, Table for 1 Inc.)

First, before you share how you feel or lack of effort you’ve observed, stop and think about the goal itself…and what strengths does your partner possess to help accomplish the goal. Next, identify a small task associated it with the goal(in your partner’s area of strength. Remember timing is everything, if you both agreed to goal and are believers you should be committed to praying about it together. So maybe one day after prayer you make the special “ask” towards achieving your goal. Finally, remember goals should be S.M.A.R.T. - Specific, Measurable, Attainable, Realistic, Timely. Sometimes we set goals but they are out of season…ask God about that too! Ultimately, at the table for ONE, with God at the center our S.M.A.R.T. goals should glorify God, edify one another and build His kingdom not just grow our bank accounts…which means its not about you two….but the power of ONE that can transform your family, community and legacy


Erica J. Holston is a Certified Relationship and Communication Coach. She has been coaching people for over four years and married for the past six years. Erica helps individuals and couples with their communication and relationship issues. If you are struggling with dating, getting along with the person you love, or communicating your needs to other people, please contact Vine Life Coaching. Erica helps people enhance their connections, build their communication skills, and create lasting change by setting realistic goals. For more information, please email

Jenise Lee is a gifted writer, speaker and thought leader. She is the founder of Over the Hump Messages where she challenges women to get “over the hump” in their professional and personal stages of life where they feel stuck.  Jenise has worked for at Fifth Third Bank for almost fifteen years, an alum of UC, and diehard Bengals fan…Who Dey!

Patrick Golston is the owner of Circumspect Life Consulting, LLC, he provides spiritual insight and participation in various Focus Groups, Think Tanks and ministries, as well as being a spiritual/creative consultant to various periodicals and websites focused on masculinity, relationships, and intersexual dynamics. 

Cory Cabri is an engineer by trade and a minister by faith. He is the author of the Christian fiction book, When I Grow Up and is the host of the podcast “Living Life On Purpose.”