Dating can be all fun and games or the beginning of a beautiful relationship. Which path you go down depends on how you test your computability early on. We often hear daunting tales from clients who have arrived at our door after staying in a bad relationship way too long. This time around they want to make sure they don’t make the same mistakes again. Having the right conversations at the start can help you get there. Bringing up the certain topics fast, at least on a surface level, will open the door to either making the decision to cut the cord or to give more attention and discussion on the issues that might need a bit more probing before you move forward. Ultimately, it’s up to you to act on the information you’ve gathered to know whether you’ve got a keeper or need to run for the hills, but in the meantime, here’s your starting guide.

First Date Topic Musts

Who are YOU?
On date one, know who you are and be able to communicate it. When he starts the conversation “so tell me about yourself” most women cringe when it comes to this question and avoid giving a detailed, honest answer. Often the reason is that we may have devoted our time to our careers or even conforming to obligations placed on us from family, friends, or even organizations we belong to. The down side of that over time however can sometimes lead to no longer having any idea of who you are. Start preparing your mind with three or four things you want him to know about you. It cannot have anything to do with career, family, or pets. Think about things like the trips you may have taken over the years, foods you like, things that make you laugh, and times when you’re the happiest. If you can’t communicate to him what’s important to you, how can he possibly know how to make you happy?

How does he like to unwind?
There’s no good or bad, right or wrong answer here. Some men figure they work hard and enjoy staying inside not looking to do outside activities. While others like to unwind with friends he might meet regularly on the golf course, a sports bar or at a sporting event. See if his answer could work for you on an ongoing basis or if it’s drastically different than what you like to do – maybe not a deal breaker initially but definitely food for thought.

Second Date Time!

Who is HE?
Learn as much as you possibly can about him. His likes, dislikes. This is an observation date. You should be focused and listen to his conversation and regurgitate specific topics that he’s shared with interest on learning more. Ask questions and give some examples of how you’ve also enjoyed some of the things he loves or that you’ve always wanted to learn. Remember men love it when you can offer feedback and solutions that he may have never thought of before.

What things stimulate him the most in a relationship?
Many of us would just assume sex would be the number one answer. But let’s not always assume that’s the only thing. Some men enjoy a great conversation or a woman who keeps herself up. Others love a woman who can switch gears from a busy day at the office to the fun girlfriend who can throw on jeans and a cute shirt and watch the game with the rest of them. Or he may enjoy hugs and public displays of affection. It will be fun to hear his answers and see if he is describing you or not.

What are his overall plans for the future?
This shouldn’t be an interrogation or interview. But try to uncover his perception of what the next year or two looks like in his mind. What are some things he wants to accomplish or fun things he wants to do? Is he happy at his current position at work or is he looking to transition into something else that’s similar or maybe a huge change to something he’s passionate about? Either way offer him encouragement, and let him know that sharing his dreams and goals with you is a safe place. It’s good idea however to take a moment to determine if where he wants to go is a trip you’re willing to take.

You’re On Date Three!

It’s time to discuss his family, past relationship history, etc. in more detail
Ask a little more about his relationship with his immediate family. Delve a little deeper into his past relationships and what he’s learned from them. Remember to keep it relatively brief, keep a positive attitude, and offer praise on his learning experiences. As you begin to share your past relationship history, express that you are in a great place in your life and thankful for the lessons you’ve learned. You can always let him know what you look forward to doing differently next time around and vice versa.

What is his view on spirituality?
Let’s face it, with 87% of the population on earth believing in a higher power, we cannot get around this topic. It’s important to communicate how involved you are in your faith, if at all. Are you someone who is ok with him being spiritual and non-religious or would you expect him to physically attend service with you on a regular basis? It’s important to know now to avoid conflicts later in the relationship.

Know your view on marriage and relationships and ask for his.
You may have grown up seeing more traditional relationships where the man takes the lead with decisions and finances. Or you may envision you both approaching everything 50/50. Since 9 times out of 10 he didn’t grow up around you, he has no idea what you have in mind that makes a solid, long-lasting relationship. So we suggest you ask what types of relationships he grew up around and how he envisions his own in the future.

Does he want children, and if so, what is his view on parenting and fatherhood?
Have you ever known someone who kept moving forward in a relationship knowing her man didn’t want children and she thought she would “love him” into changing his mind? Ladies take him at his word. On the other hand if he does want children, ask what parental roles he saw growing up and what he would like to mirror or maybe do differently when it’s his turn. Overall, if both of your views on having children or parenting turn out to be in sync that is a major plus.

What are his thoughts on sexuality?
Yes we know this subject can be a bit uncomfortable, but the truth is, sex is one of the most important connections, and sometimes downfalls, in a relationship. It’s important to know each other’s expectations and what you both describe as healthy sex. Without probing too deeply by date 3, there are ways to find out things like whether he feels sex is for couples that are monogamous? Or is it ok while you’re both still getting to know each other and dating other people? Or is it reserved for married couples only and even then, what does he envision? You will certainly hear a few buzzwords in his explanation that will let you know whether you’re both on the same page.

What is his view of money?
Some men have been raised to feel like they should be the provider for their household. Others may have been hurt or used in the past and more guarded about sharing finances when in a serious relationship or marriage and have more of a “what’s mine is mine and what’s yours is yours” philosophy. With finances being one of the top reasons for failed relationships, by date three we would suggest you have an overall understanding of whether your views on finances are at the very least loosely aligned. You can always get into more detail in subsequent dates.

Here’s to LOVE!!

The Matchmaking DUO