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How to Know if You Should Keep Trying with Him

Have you ever wondered what the right amount of effort to put in with a guy is?

You may have heard me say, “Invest in those who invest in you.” But that could leave you wondering to yourself: “Doesn’t someone need to take the first step to invest something if anything is ever going to happen?”

It’s a valid point. I’ll show you exactly how to solve this at the end of the video, so make sure you watch it through…

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So last week, I ended with the conclusion on a bunch of terms like ghosting, zombieing, haunting that they all just represented low investment and, therefore, were all indicative of a central problem, which was that we tend to invest in people based on how much we like them, not based on how much they are investing in us. And I’ve said this ad nauseam over the course of the last decade of my life, the people that follow me a lot will be able to repeat this phrase easily, because I say it so much: Invest in those who invest in you. Don’t invest in someone based on how much you like them.

But there is a challenge to this that I think is interesting because it adds a little nuance. Someone could easily say, “But Matthew…” and by the way someone did say this. I was on a podcast with Lisa Bilyeu on her Women of Impact podcast. I am not a woman of impact, but I graciously was allowed to come on the podcast as an honorary male. She said to me upon hearing this, “I love that, but doesn’t that get you into a kind of standoff with someone where you’re both holding your gun, waiting for the other person to draw before you do anything? Can it lead to a situation where relationships are simply transactions, where you wait for somebody else to invest before you do anything at all?”

This is where a principal comes in to temper this idea: We have to invest and then test. This is something, a phrase that my brother Stephen Hussey, who writes for our website, HowToGetTheGuy.com, coined. Invest then test. In other words, give a little, and then see if they move a little to meet you where you are.

I think about this from the first moment you meet someone. You see someone in a coffee shop, it’s like, maybe you both are attracted, you both want to talk to each other. One person at some point has got to make it easier on both of you, right? Someone has to take responsibility for making it a bit easier.

So what happens? Maybe one person goes and sits close to that person, right? I know we live in a world now where the idea of going and sitting close to someone seems like a thing of the past, what an anachronism, but let’s just take the concept in. We have to be able to talk about normal things sometimes, my God, if only to illustrate a point. You go sit somewhat close to that person. That person thinks, “Oh, the person I was making eye contact with is now sitting kind of close to me.” Now one person says, “You all right? I like what you’ve ordered there. It looks delicious.” And then, “It is delicious. I’ve had it before. How are you? What’s your name?” Now you’ve got a conversation that’s happening because both people, they put in a little bit, put in a little bit.

Sometimes in the beginning, one person has to overcome another person’s shyness and do something a bit more drastic. Go over and just start talking to them because this person is never going to come over of their own volition.

That happens at that stage. Then there’s the later stages of, okay, when we’re in the texting phase, I need to look and see, as Jameson and I have talked about previously in a video, am I in the blue?



Simmi Singh:

We text all the time.


Matthew Hussey:

Simmi, the colors, look at the colors. You’re in the blue, mate.



When I send them meaty messages where I actually say things, do they send me quick one-word or three-word answers? That’s a form of taking a leap of faith that, while I like someone so I’m going to let them know about it and I’m going to see how they respond, but then actually paying attention to the response. Is the investment equal or do you always feel like you’re the one investing a lot more than that person is? Invest, then test. I don’t mean test in the manipulative, game-playing sense. Simply measure what’s the reaction.

In dating in general, I think one of the big problems is we don’t do enough communicating, but we do too much chasing.

Communicating is letting someone know that you like them. “I find you attractive. I’d love to hang out sometime. We should go for a coffee,” or, “I’m into you. I like something about you,” or, “You look cute in that top,” or whatever. That’s communicating. What I’m doing there is showing that I like you.

Chasing is when you continue to invest in someone, you continue to keep chasing them, to keep giving them energy long after the point of having already communicated that you like them, and without the equivalent return of attention, of interaction from them. That’s chasing.

I’m a huge proponent of communicating and someone who’s trying to stop people from chasing. When I say invest in who invests in you, it’s not about always waiting for someone else to make the first move. Investing a little bit so that someone knows where you stand, so that someone knows that you like them, so that someone knows you’re open to a date, so that someone knows that you’d like to see them for a second date, so that someone knows that you find them attractive, sexy, appealing as a human being: That’s brave. That’s vulnerable. That’s courageous.

Chasing someone is a sign of low self-worth, losing our own self-respect and having put someone on a pedestal. And I say put someone on a pedestal because how can someone be so great that you continue to chase them when they’re not giving you that back? No one can be that great because greatness, someone who’s great for a relationship with you, doesn’t just come in the form of someone who’s got great qualities, it comes in the form of someone who represents a great energy in your life, represents a great investment in you as a human being. You can’t have one without the other. You can’t have someone who’s great for a relationship, but doesn’t invest.

So chasing is chasing someone who you admire, who you think is great, but someone who ultimately is not actually investing in building something with you. Invest a little so that you can test whether you get anything back. And only continue to invest in those who invest in you.

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22 Replies to “How to Know if You Should Keep Trying with Him”

  • Awesome! As you say, it’s a delicate dance, a little cha, cha, merengue or macarena. The best part is, these dances are great solo too, irregardless! ;-)

  • I just love your advice. It comes in very handy at this stage in my life. Although I still some days feel i should text him…i stop and think about whether I’m the only one investing…thanks for the great advice xx

  • Matthew… please do a video on how LONG a woman should invest in response to his continued investment. For example, what if she wants marriage someday and he is unsure if he wants to marry again, but he’s showed all signs of commitment, investment, and says the right things. How long? A year, 2 years…? We all know 5 or 10 years as a girlfriend is TOO LONG. But where’s the cutoff point of decision??

  • Does the same rule “invest in him, only if he invests in you” apply to a man who you have met on a dating website and have not seen him yet in person. By your definition, I am aware now that I a actually chasing that man, but I was still wondering if there is a chance that things will change if we once meet.

  • Can I just say, Matthew, that you offer some of the best value, and most valuable wisdom, available on the internet. Class act, as usual. And thanks.

  • Wow! Thank you Matthew. That is really profound and has just really clarified things for me on this. Communicating how I feel has always felt like “chasing” so I have avoided it. But to communicate how I feel and THEN see what happens and take heed of that and only invest more if there is some investment comes my way. That suddenly seems like relationship advice that makes so much sense. Thank you so much. Helen :) x

  • Point well-taken, Matt! Another great video!! I see a girlfriend of mine doing something in her relationship, that I recognize as something that I have done at times as well, that I and wondering if you could address in a future video. It’s when you realize the other person isn’t investing as much as you, but your ego gets involved, and you set out to prove to them that you’re worth investing in. It sets up a vicious cycle of being stuck in an unfulfilling relationship, because you can’t walk away because you want the other person to acknowledge that you’re worthy at some level. I think it’s something that a lot of women fall prey to, and I’d love to get your take on it, and how to dig your way out instead of wasting months or years in that state. I know you have addressed several angles of this in your work over the years, but wanted to present it to you in this way because you are so good at articulating things and helping me see things in a new way! Thank you, Matt, for everything you do!! It’s how many years now since I first found you on Ready for Love, and I still learn from you on a regular basis!!

  • I just had an ahhhhh haaaaa moment, when you said [they] represent a great energy in your life”
    This isn’t just an assessment I can hold for my own life, but also one that I can hold for my presence in other people’s lives too, am I a great energy, and if it’s not mutua, then change it or back away!
    Thanks Matthew and team, the last few months of dating would have been very scary without your advise. Keep up the good work.

  • I need help. I’m 62 and have been divorced for 6 years. I started dating a guy when I was separated and now have been with him for 6 years. He has never been married but has had numerous short term girlfriends. He also has a grown son. His family all loves me and I go to all his family functions We go on trips and hang out all the time but he will never commit to a future with me. I have always been the affectionate one letting him know how I feel but always feeling I get no affirmation. He has stopped being physically affectionate and we barely have any physical touch. I feel empty and lonely when he leaves . He asked me not to long ago if “ we are just desperate or pathetic “ . I am so hurt by his lack of love.But it’s confusing because he comes over and does nice things for me , helps me through a surgery I had and helps me around the yard and the house if I need things done. So I am confused by his intent. I don’t know after six years if this man loves me. I told him at one point that I am thinking of moving to Florida and his reply was “ I’ll come visit you” . This is breaking my heart and I don’t want to break up but I don’t know if maybe I should? Please help . K

  • Great material, thank you Matthew.

    BTW, total aside, you must be working out in quarantine/COVID times. Your arms are HUGE! Good job! LOL!

    That’s inspirational in itself!

  • I think this is among the most significant info for me. And i am glad reading your article. But want to remark on some general things, The website style is ideal, the articles is really great : D. Good job, cheers Christabella Harland Belsky

  • I have read a few good stuff here. Definitely worth bookmarking for revisiting. I surprise how much effort you put to make such a fantastic informative website. Kyle Ivan Weinstock

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