How To Have ‘That’ Conversation

Wow, this guy connects with me on so many levels. We like the same movies and books. We have passionate, romantic sex. We can talk for hours and both care about family.

It’s never felt this good before with anyone. I feel I can really be myself and relax around him. 

But is he looking for this to go somewhere? I don’t want to blow it. How do I ask him if this is for real, or if it’s just casual fun for him…

*     *     *     *     *     *

It’s difficult in the early dating stage to know when it’s time for the relationship talk.

You may have a guy who seems to make a ton of effort, who says you’re like no woman he’s ever met, but you still haven’t had the BIG conversation to define yourself as an exclusive couple.

couple smiling in bed

In this article, I’m going to make this part of dating a lot easier. This shouldn’t be a cause for high anxiety – it should be just a natural step that you approach as you get closer to a guy.

But that being said, timing does matter here.

So to begin, before you ever have the relationship talk, it’s important to first know the signs that a guy is thinking about a relationship so that you don’t waste your time.

Signs A Guy Wants A Relationship (Or Just Casual Dating)

man thinking about love

So, unfortunately guys don’t walk around with a sticker on their head that says, “I’m looking for something serious with you”.

How do you decide then whether this is just a bit of casual fun for him, or whether it’s just a matter of time before he asks you to be his girlfriend?

Luckily, guys aren’t that subtle. You just need to pay attention to five crucial signs that will give you a clue to his intentions:

  • He wants to see you at least once or twice a week.
  • He initiates texting or calling on a regular basis.
  • He doesn’t say things like “I enjoy being single right now”.
  • He spends quality time with you (i.e. not just “booty calling” you to come over late at night on the weekends).
  • He casually talks about plans involving both of you in the future (e.g. trips and vacations).
  • He asks about wanting to be sexually exclusive.

If you see at least 4-5 of these signs, then it’s safe to say that things are looking pretty good for you both moving towards a relationship.

However, it’s crucial that you never just assume that you are exclusive with a guy. This doesn’t mean you need some huge conversation, but you do need to feel open enough to raise the subject of “What are we?” and have a frank discussion about it.

Until you’ve had the relationship talk, never just assume it’s official.

I’ve seen many people over my years of coaching who get hurt this way and waste months or years with the wrong guy because they never brought up the conversation of defining what they wanted the relationship to be. Don’t make that mistake.

The Male Approach To Defining The Relationship

man kissing woman

Typically, men will be a little bit slower than the average woman in terms of how fast they move the relationship forward (though not all guys – some guys will move far quicker than you are comfortable with – these “impulsive romantics” are also guys you should be wary of).

In general, many guys begin dating a woman not 100% certain if they want a relationship or not.

Some guys are committed to their single life, other guys date with the attitude of “If I meet an amazing woman, then I’ll have a relationship”.

If you have the latter guy, then you want to be very keen to observe how much effort and attention he is putting into your dates.


  • Does he try to come up with fun ideas for places to take you?
  • Does he put real time into seeing you?
  • Does he want to introduce you to his friends and bring you places with him?
  • Is he affectionate in his words and actions when you’re intimate together?

Look at these behaviors, and listen to your gut, and you’ll have a sense of whether this guy is truly pursuing you or whether he just sees you as someone to date at his convenience. Give it a few weeks or a month of dating so you can see his behavior over a period of time, rather than judging him on a single week.

Tips For Having The Conversation – How To Define The Relationship

couple talking in bed

So, assuming you’ve read the above and you’re thinking to yourself, “Yep, this guy is definitely into me and seems to want more”, then now you need to be ready to have the conversation.

There are three steps to this:

Step 1 – Be clear, but don’t be intense 

You should be able to talk about this in a very comfortable and matter-of-fact way.

This takes confidence, but it’s crucial you enter with this attitude so that you can be honest and make it clear what you want.

So simply say to him, “I’ve been having a great time with you, and I just wanted to know if you see this as being exclusive? I’m not asking for a decision this second, but it would help to know what you’re looking for.”

This is a great low-pressure way to find out what he’s thinking in no uncertain terms, and gives you a chance to react accordingly based on his decision.

Step 2 – Let him speak his mind

Now, give him space to express whatever his thoughts are.

Listen carefully here. If he’s into you, he’ll talk about how he only wants to see you and doesn’t want you to see anyone else. It’s also a good sign if he says anything about wanting get closer to you, or if he expresses a desire to be in a relationship.

But if he says things like:

  • “I just want to enjoy myself right now.”
  • “I’m not looking for anything too serious.”
  • “We’re just having fun.”

These are all clear expressions that he’s not thinking about being in a relationship, and you should begin to make plans to cut things off (if you’re looking for something serious) before you get in any deeper.

Step 3 – Make him know you won’t wait for long

What if he says he would like to be exclusive eventually, but wants to wait for a while before deciding?

In this case you should be understanding, but make him know that you are someone who will move on eventually and won’t settle for being in relationship limbo.

For example, you might say, “That’s ok, but just so you know I don’t do the whole casual dating thing. So if you don’t want anything serious, I think we should leave things for now until you know for sure before we get in any deeper.”

In other words, be the one who lets it go.

When a man knows you are willing to let him go if he doesn’t make a decision, you will find out much faster what he really wants deep down.

Either he’ll let the relationship fizzle out (in which case, it’s a good thing you ended it now before you wasted a year of your life), or he’ll take a couple of days or a week to think it over and he’ll pursue you and tell you he wants to be exclusive.

Whatever happens though, know your value and don’t settle for less than your worth. If a guy isn’t willing as least consider exclusivity after a month or two of dating, it’s time to move on and find someone who will.

Want to learn 59 more REALLY simple conversational flirting techniques to get in a guy’s head and make him crazy for you?

Must Watch: ‘The Phrases That Make Men Beg to Be With You’

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13 Replies to “How To Have ‘That’ Conversation”

  • Whoa! I needed this!
    Yes, he is so passionate, he is cute and treats me kind, more than the other boyfriends treated me…
    But I’m not feeling clear about what kind of relationship we have…
    I will practice and apply! ;)

  • Great article with such clear structure on finding a partner. There is however something that I have been looking for an answer for long and couldn’t find it , would you kindly share your view in this matter –
    What is the best way to handle infatuation and does it ever have the potential of becoming fulfilling lasting love? It is almost always a sign of life changing growing time when it happens – wether being the infatuated or the one being on the pedestal. How long does it take to know that it is real love or infatuation? Is infatuation always short-lived?

  • Hi Matthew,

    I had been in love with my very best friend for at least a year and thanks to all your advice and blog posts we have been dating for 8 weeks (and the chemistry is off the charts) and last night we had that conversation. We went from “we are just friends” to “I think I can imagine spending a long time with you. ”
    i didnt have to start the conversation, all I did was to set the direction a bit.
    Being a woman is sometimes hard. But doing it right, treating myself the right way, keeping my own life has felt so so so good.
    Thank you! I am not scared that I won’t keep the guy. And am so looking forward to building up a good relationship.

  • What is exactly a “impulsive romantic”? I understand what it means, but I’d like to know a more indepth understanding.

  • I’ve been dating a wonderful man for about 5 months. We have strong attractions to each other both physically & personality wise. We are also very compatible sexually. Many people, who we both know and spend time with, have commented on the chemistry that is apparent when we are together.

    However, we both made one huge mistake. While we didn’t immediately act upon our feelings, we didn’t have this conversation when we should have. He didn’t want to mess up a good thing & I was too afraid to hear the answer. After seeing he was still active on the dating site we met through, it became very clear we needed to have this conversation immediately. We both agreed in person was best, so we met at my house.

    During our talk, we both agreed that we should have had this conversation many months ago. It was revealed that he is not sure what he wants or if he’s even ready for a relationship after his recent divorce & I now know where he is emotionally & I understand why. He now knows that when physical intimacy is involved, I expect to be in an exclusive relationship, & he says he understands & can respect that. Sex was absolutely taken off the table.

    While it’s more of a challenge for me to adjust emotionally to this information, for now, I’m ok with the decision we made to continue to see each other. I don’t know where this will lead, but the fact that he really isn’t going to be “getting anything” from me any longer, the communication level has not changed, & he still wants to see me (and has) is hopefully a positive sign. In my experience, removing physical intimacy would be an absolute deal breaker for many, if not most, men.

    I don’t know if I’m making the right decision by continuing to see him under these circumstances, but he is not a player & I trust he is & will tell me the truth. With that said, I took a line from another video of Matthew’s & told him I hope I’m still around when he is able/does make a decision to be in a relationship. In the mean time, I’m taking tips from other videos available to improve my dating skills to find what I am looking for.

    His response completely threw me for a loop & I’m still not sure how to wrap my head around this one….

  • when I had this conversation he gave me the answer of I’m not saying anyone else right now. He later tried to say that it that was his way of saying that we were exclusive but I think there’s a big difference between saying I’m not dating anyone else right now and I’m only interested in seeing you. It’s like saying I’m doing this until something better comes along. What do I say or text to spress at this is not okay

  • Why would anyone start dating a guy without being exclusive? Why would I start seeing a guy who meets other women? How could someone take a guy seriously or consider spending any time with him, while not being sure she is exclusive? People have not enough self-esteem here? Why is this an issue at all? If a man approaches you as you may be casual for him, dump him on the spot, except if this is what you want as well! Most of the time I was seeing someone who told me at the beginning what his intention was. If a guy does not know what he wants at all, he may not show enough respect or does not have enough reason to consider going out with. Most men told me: “Trust me, we all know/consider what we want from a woman within 20 seconds after meeting her.”

  • I was introduced to a guy last year February,2017 by a mutual friend and he really seemed like a nice guy. At that point in my life I was not dating anybody so we decided to be friends and start from there. Though he was an introvert and quite reserved I liked him because 2 guys I dated previously were extrovert and fun guys. I decided to give this grounded guy a chance. He was sweet from the beginning, sent flowers to my office every week, bought me gifts of any kind. He was a good listener and could watch me talk his ear off. he spoke little of himself and family. I figured once was very comfortable he would open up because I saw him to be very protective and guarded about his family and friends. I was never introduced to anyone.. He asked me to be his girlfriend in March and I agreed. We had so much fun. He said he loved me almost immediately we met but I froze because it was quite early. I didnt say anything back but I explained my reservations of past experiences. We continued dating, he would text me call me and want to pick me from work even though we lived at opposite ends of the city. I sometimes allowed him to pick me because I felt he was lonely. He had no family in the country, they were all abroad and had very few friends.

    Fast forward he started talking about marriage and wedding and cost of items and stuff like that. He would talk about how many kids he wanted an all that. He even asked when I wanted to get married and I replied 2018. he said OK. We started looking at lands and property for him since I was an architect and would provide the necessary advice. Because of his energy of interest in marriage I asked him when he wanted to start counseling since we were both Christians, he said he was not in the mood to talk. I asked him the next week and he still shut the conversation down. I was beginning to sense something. He apologized a month later that he was afraid of weddings. I told him we could do something small, a quiet garden wedding of some sorts. he did not acknowledge so I stopped talking about marriage and weddings to put him at ease.. I realized he started pulling away. he would hardly call or text and when I do so he was either busy at work or with a program. I realized I was the one doing all the calls texts and visitation. I moved to another part of town and its been 3 months he never came to see where I lived with my family.Prior to that I told him I want to talk to him about something bothering me and he replied that he would make time to talk when he was free. its three weeks now. I visited him again and he was not welcoming. he avoid the hugs and kisses I wanted to give him. I told him when he was free he should call me to talk and left his place.

    I called the friend who introduced us and told her everything. She called him just to make friendly talk and anytime she brought me up in the convo he avoided talking about me. She asked him if he had introduced me to his mum and he replied no, not yet. Rori, I couldnt believe this because I have screen shots of messages he sent to me about his mum wanting to meet me. Truth be told anytime I want to chat with his mum but he always he replied not yet, soon. I knew something was up but I did not know he had not told his family about me the whole year we were dating. I feel like I have been living in a lie bubble. What hurt me the most was our mutual friend told me he was at my dad’s funeral the previous year, we had not met by then, and was friends with my step sister but he failed to mention it even though its been 2 years already. I am not sure if he wanted to date her and it didnt work out or something. But I think he should have told me he knew my step sister.

    I was shocked at all this revelations of him keeping stuff from me. I found his mum’s number on social media and am tempted to call and make enquiries about her son. I called him again to ask for a sit down but I got the same reply, when he was free he will let us meet. I have decided not to call him for a few weeks to see if things will turn around. If not, I go my way… the sad thing is my family think we are settling down this year.

    I really need help on my next move

    Sorry for pouring out my heart in this long letter.


  • Hey Matt I love your videos but I have noticed that most of it is for relationship looking purposes. Although, Women could also be in a place in their lives where they’d only settle for causal relations. Could you please touch up more on how to go about having a healthy casual encounter. And what we can do to say no to some things if we’re not into our partners sex style without actually ruining the casual relationship. Help Matt!!

  • This is absolutely perfect! Ran into this exact situation and I said basically this, but your wording was much better. Will definitely use this in the future

  • I’ve been dating a guy for 6 weeks. I told him I’m not intrested in seeing anyone else, but him. He told me he is enjoying spending time with me, but is also dating other people. Should I let him go? Please help

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