How Long Do I Wait For A Man Before I’m Wasting My Time?

I’m 30 years old, divorced with no kids, smart, pretty not only on the outside but on the inside too (so people tell me,) very family oriented and have great values. I’ve followed your advice from A to Z and GOD HAVE THEY HELPED!!!! But now I’m extremely puzzled and need your advice. Less than a month ago, I started dating a guy who, according to my mother, I shouldn’t even be dating because he’s “way too good looking” and “guys like that” don’t like to be in steady relationships.

Anyway, I try to think about what you’ve said about your wife, how at the beginning she wasn’t the type of girl you were used to dating… And I’ve followed every step you talk about when it comes to her, “to be cool, calm, and collected…”

From day one, this guy and I had a great chemistry, in the sense that we truly enjoy each other’s company. He is the one that calls me (even if I’m like dying to call, I wait for his call,) he is the one that talks about seeing each other and so on… (No sex yet, as I want to get to know him a little better.) Well, last night he told me that he’s starting to genuinely like me, and that concerned him, because as perfect as that is, it’s not a good idea…. (As far as I know, I’m the only person he’s dating.) He told me that it wasn’t supposed to happen that way nor was he supposed to feel so comfortable around me!

So my question to you, Evan: Is this normal? Or is this a red flag? I really like this guy and don’t want to mess things up!  So I just smiled and avoided getting too deep in the subject as I noticed he was a bit stressed over it. I remember what you said about your wife, that she never asked where you guys were headed… I know you are super busy, but I’ve come such a long way, and I’m so proud of myself with all the changes I’ve made since I started reading your newsletters, that I don’t want to do or say the wrong thing here. What does it mean when he said that? Thank you soooo much and may God bless you, your wife and your beautiful baby that’s about to come!!!! —Mari

Dear Mari,

Thank you for your very kind words. I’m genuinely thrilled that you’re seeing positive changes in your love life since you started reading. And I chose your letter out of the hundreds of emails I get each month because I find it infinitely more challenging to take on a situation that is not at all black and white.

In fact, I’m guessing every one reading this has been in the exact same position as you, with the same exact question:

“How long do I invest in a man before I panic that I’m wasting my time?”

Believe the Negatives. Ignore the Positives,

And try though I might, this isn’t something that can easily be reduced to a simple science, because each individual man has his own unique set of issues.

What I will remind you is of the newsletter that I wrote less than six months ago, which proclaimed, “Believe the Negatives. Ignore the Positives.”

What I meant by that is that millions of women have willingly entered into passionate affairs based on their feelings alone – the breathless waiting for his call, the physical need to touch him, the giddiness he inspires when you’re together, etc – all the while, conveniently ignoring the fact that he said at the very beginning, “I’m not looking for a relationship right now.”

So he feels like he’s off the hook because he told you the truth at the outset, you forget that he doesn’t want to be anybody’s boyfriend because of how you feel when you’re together, and one day, when you start to wonder where things are going, he reminds you of that conversation you had in your first week where he laid down the law.

…you forget that he doesn’t want to be anybody’s boyfriend because of how you feel when you’re together.

Every woman who proceeds to date a guy who “isn’t looking for anything serious” is essentially driving over the orange cones and through the yellow tape that signify danger, and wondering why she always gets into an accident.

You ignored the warning signs, such as “I don’t want a girlfriend.” What did you expect?

This isn’t a matter of defending guys who date you even when they’re emotionally unavailable. This is merely pointing out that it happens ALL the time.

You’re Ms. Right Now, you want to be Ms. Right, but he’s not currently taking applications for that position.

Then why does he act so open? Why does he call me? Why does he treat me so well? Why does he hint at a future?

There are a couple of very reasonable answers to this question, but the primary ones are:

1)    It’s in his best interests to treat you well. What possible purpose would it serve for him to be rude to you? Do you think that’s a proper way to treat somebody? Of course not. So he calls you (because he wants to see you), he sleeps with you (because he’s attracted to you), and he talks about falling in love one day (because he wants to fall in love one day.) It’s completely possible to do ALL of these things and still not want to have a serious committed relationship right this second. And that’s what you’re seeing over and over.

2)    He doesn’t KNOW what he wants. You should understand this, because half the time, YOU don’t know what you want either! Do you want the exciting guy who leave you breathless? The safe guy who treats you like gold and always lets you know where you stand? Do you want wild, unattached sex? Or to date around to explore your options while you focus on yourself and your career? Confusion and ambivalence are human traits, not just male ones. He may very well feel that he’s not ready for love right now…and still legitimately be falling in love with you.

So what do you do, Mari?

You take it all in. You don’t make any rash decisions. You let him reveal himself in his actions and not just his words. You continue to be the woman that no man can leave.

And you pay attention to the signs that he’s not ready – his anxiety, where he’s at in his career, how old he is, whether his friends are happily married, what he wants in the long run. If you see too many red flags, you get out.

But if you’re happy and he’s happy, he may just be adjusting to his new reality – that he IS ready for love…with YOU. Give him a chance before you bail on him. The only way it can happen is if you let it happen, not if you pull the plug.

Join our conversation (51 Comments).
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  1. 1

    This guy is bad news. He’s a manipulator and messing with your head. Dump him before he breaks your heart. It’s good you haven’t had sex yet – could’ve been much worse

  2. 2

    Well, last night he told me that he’s starting to genuinely like me, and that concerned him, because as perfect as that is, it’s not a good idea…. (As far as I know, I’m the only person he’s dating.) He told me that it wasn’t supposed to happen that way nor was he supposed to feel so comfortable around me!
    If I was dating a man and he told me that, I wouldn’t sit back and smile politely, I would ask him to explain what he meant. Perhaps Evan’s wife never asked where they were headed, but did Evan make such comments to her? My guess is no. If you are not clear about something a man says, ASK! It’s your life, your future, and you are not pressuring him, you are asking him to clarify something that HE brought up.
    Also, your mother isn’t exactly instilling you with confidence when she says this man is “way too good-looking” to be serious about you.

    1. 2.1


  3. 3
    Christie Hartman

    Nah, it’s too soon to tell. Not all red flags turn out to be problems. I say take it slow and wait for him to screw up (or not to).
    And I could not agree more about paying attention to the negatives. I just told a young woman basically the same thing in my blog – when the messages are mixed, the bad ones are the bottom line.

  4. 4

     Rule #1:   Don’t take dating advice from your parents.
    Well, last night he told me that he’s starting to genuinely like me, and that concerned him, because as perfect as that is, it’s not a good idea…. (As far as I know, I’m the only person he’s dating.) He told me that it wasn’t supposed to happen that way nor was he supposed to feel so comfortable around me!
    Um, that is the sort of the WHOLE IDEA behind dating.
    Red flag time.

  5. 5
    Aimee S.

    Doesn’t matter how much a man likes you or is attracted to you, if he doesn’t want a girlfriend, he will not have one.  Can he change his mind? Sure. But it’s unlikely. I was just there and told the guy it wasn’t working for me.  I think he was shocked. If he ever wants to call me again he knows it has to be if he wants a serious relationship – or to see if one is possible w/ me.  I know he won’t call. Cutting your losses is less painful than heartbreak.

  6. 6

    What does this woman want – an STR or and LTR/Marriage?  Why is an STR a bad thing, its a learning experience, you have fun, its part of dating.  But if she doesn’t want to casually date, don’t sleep with him unless you are both committed to marriage, wait months or years before sleeping with each other if needed.  Plan C, just get off the pill and have an accidental baby out of wedlock, especially if he’s rich, he’ll pay the child support.

    1. 6.1

      Get serious Joe boy!

    2. 6.2

      WHAT kind of advice is that!!! My mother got pregnant. My Dad married her. Had two more kids. Divorced. Basically screwed up 5 people’s lives!!! The worst advice you can give anyone!!! I tell ALL of my guy friends to use condoms for this reason!

  7. 7

    Okay. This is really confusing. Isn’t the idea of dating to hopefully find someone you genuinely like? If that’s not a good idea, what is? His comment that, “it wasn’t suppose to happen that way nor was he supposed to feel so comfortable around me” is perplexing. Again, is it better to feel tied up in knots? Maybe the guy’s accustomed to a lot of drama girls or maybe he’s starting to fall fast and it scares him. Maybe he’s afraid of intimacy or he doesn’t think it’s a good idea because then you’ll want to get all married and stuff. Maybe he has another girl on the side or unfinished business in his past, and he’s realizing that he’s starting to create an emotional mess.
    The reasons why don’t really matter. In hindsight, I would have suggested that you respond to his comments by smiling and saying how much you genuinely liked him, too, and could he please explain what he meant. I’d bide my time a bit longer, but not too much longer. Whatever is happening in his internal life, his insecurity and unsureness may lead to heart break later on.

  8. 8

    @Joe:  Actually, Plan C never works. Plan C is a high-school manuver. Classy women don’t DO plan C.  So why even bring it up here?

    1. 8.1
      Charlotte C.

      True,plan C is stupid

  9. 9

    A month is nothing.  A speck.  Watchful waiting is the key at this point.  Go out when he asks if you’re available; look nice, smell nice, be nice, have fun, then go home and evaluate what you see, hear and feel on your dates with him.  Keep doing what you’re doing – which is not sleeping with or pursuing him – and I would add in, date other men while you’re at it.  If he said he doesn’t want a girlfriend and you’re not sleeping together, why be exclusive and limit your options?  If you’re serious about finding a LTR, then don’t stop looking now just ’cause you met someone cute.  And it could very well be that Mr. Handsome, who probably isn’t used to dating such a self-assured, self-possessed young lady, might just change his mind about whether or not he’s “ready” for anything more if he scents a faint whiff of competition on the breeze.

  10. 10

    “It’s not a good idea… wasn’t suppose to happen that way…”

    I think it’s a game. He wants you to work harder to push him over that edge he’s hinting about. The “I’m unsure and suprised by my feelings for you…..” edge. He wants you to think, “okay, I’ll seal the deal with sex.” And soon after, he’d probably fade.

    Don’t have sex with him. Major red flags. If you want to give this more time, do so without sex and start dating others so you don’t get too swept up in this one person.

  11. 11
    Katarina Phang

    Give him a chance but keep your options open.  That’s what I’m doing as well with a man I’ve been dating the last 5 months.  We’re not exclusive yet and taking things slow but everything has been positive and wonderful.  Like Evan says, be a woman he can’t leave.  I am that woman right now for him.  When I’m not with him, I’m taking care of myself and just focusing on me and my own happiness (dating and keeping busy with work/projects).

    1. 11.1

      its a lot and the way you gave me a chance
      got it

  12. 12

    Mama may be right; this dude may very well be too good looking to settle down.  She may not have used the most finessed way of wording it, but she probably has some wisdom in that area.  I would say Mari, that if you decide to wait it out a bit longer, do so with your eyes wide open.  Continue to be charming, flirty, and fun, but I’d be very careful about handing over my heart. 

  13. 13

    I totally agree with BeenThruTheWars’ #9.  Apart from his enigmatic comments, he’s been doing the right thing.  So let him keep doing the right thing until it turns into something permanent, or until he stops doing the right thing and the relationship is no more.  And if he makes any more cryptic comments, I would definitely ask for clarification on what he means.  That’s not pressure, it’s being an attentive listener.

  14. 14

    Christie Hartman
    when the messages are mixed, the bad ones are the bottom line.

    Well put!  Suitable for putting on the refrigerator.

  15. 15

    I agree with BeenThroughTheWars @ 9. A month is nothing. I´d wait another month or two, and keep doing what you´re doing, evaluate, keep your options open and if in three months he´s still not sure, then dump him. But I think dumping him now is too soon.

  16. 16

    If you’ve been dating less than a month, then I think you should hold out a bit longer. But at the same time you should not be putting all your eggs into one basket – date other people – as you’re not in an exclusive relationship… I do not want to promote false hope here but may be he did not expect to fall for you and he needs a little time (and no I do not mean months on end) to process this all and figure out how to move forward… So give him a little time and an opportunity to step-up and if he does not, then at least you will not look back on this in the future and wonder what if… At least you tried.

  17. 17

    Since these letters are printed 4-6 weeks after they were first sent to EMK, I’m wondering where things stand now – a little further along. Mari?

  18. 18
    Karl R

    Mari asked: (original post)
    “Is this normal? Or is this a red flag?”
    “What does it mean when he said that?”

    It’s certainly not a common thing for a man to say. I don’t know what he meant. And it sounds like a red flag to me.

    However, a red flag is a sign of a potential problem … not necessarily a problem in itself.

    When I first started dating my girlfriend, she told me that she wasn’t interested in a serious relationship with me, she was interested in a serious relationship with someone else, and that I was too young for her. I’d call that a red flag.

    In a relationship, it’s useful to take stock of things every three months. Things may ebb and flow from day to day, but you can usually see some significan’t progress over a three month timespan. If you can’t, that’s significant.

    By the time three months rolled around, my girlfriend had changed her mind on all three of those issues. If she hadn’t changed her mind, I would have pursued other women.

    Mari said: (original post)
    “Less than a month ago, I started dating a guy”

    It’s too soon to know anything for certain. If you like the guy, wait until the three-month mark.

    But you might want to ask what he means the next time he says something like that. You can even question it in a bantering tone. As others have said, dating someone you like is generally the point.

  19. 19

    Karl R: “When I first started dating my girlfriend, she told me that she wasn’t interested in a serious relationship with me, she was interested in a serious relationship with someone else, and that I was too young for her.”

    Why did you continue to date her?

  20. 20
    Harriet Bond

    Hmmm. Think we have all ignored these obvious red flags before and put up with vagueness because we really feel a connection with someone, and some of us have not pursued the conversations we really need because we suspect it will make them feel ‘uncomfortable’ to talk about it; but how about YOUR discomfort at NOT talking about it? You need to put yourself first, because he certainly isn’t!

    1. 20.1

      Harriet, very well said. My thought indeed… why not asking “then what do you want” and actually that is something that I would have asked from the get go. They may lie but if you are good at reading body language, tone of voice etc you can clearly see they are lying (saying for instance they want a relationship when they do not)

  21. 21

    EMK came through with another good post…

  22. 22

    I think Karl R.’s example is perfect.
    It’s funny that people will cut and run because they want guarantees that everything will work out, but life never works that way.
    I like the advice to proceed with caution, give it a decent but not ridiculous amount of time if it isn’t going anywhere (for example, you are dating someone who wants kids when you don’t, or you are dating someone who WON’T stop searching for someone else), and see what happens.
    I wish everything could be painless and didn’t involve risk but nothing is like that short of perhaps taping yourself in a cardboard box and staying at home alone forever.
    While it might suck that someone is somehow disappointed that he likes you so much, see what happens and then move on, because I think that many men and women have found themselves really attracted to someone that we weren’t “supposed” to like for one reason or another. So perhaps this means that in some way (which you need to see if you can get explained), you don’t fit whatever ideal he had in his head.
    Isn’t that true of what a lot of people end up with?  (Including the owner of this blog?) We don’t always know what we want, and more importantly, we have trouble figuring out what is best for us and what things that we want we might want to dump from the list.
    So it could still have a happy ending but you’ll know in a couple of months if this is worth pursuing.
    And I agree with someone from before who said not to listen to your mom…look, moms can be jaded, but more importantly, they want to protect you from being hurt.  Just because someone who was “too good-looking” may have done her wrong doesn’t mean that every good-looking guy hopes to be a player for life.  Don’t cut off your nose to spite your face because I’ve experienced moms who encourage people to dump people who wound up working out really well (including a recently engaged friend whose mom was trying to tell her that he wasn’t moving quickly enough, even though said friend had told him to take it slow because of her own recent divorce).
    At the end of the day, out of all of the reasons to dump someone, being too good-looking is pretty silly.  Beauty is subjective and you should assume that someone dating you considers you to be good looking enough. (And I’d hate to have friends and family tell me that I’m too plain for the person that I’m with.  Ouch, shouldn’t they be the ones telling you that you are cute?)

  23. 23
    Karl R

    jrd asked: (#19)
    “Why did you continue to date her?”

    We started dating on a cruise (we were with a large group from our dance studio). Of the available men/women in our group, neither of us was interested in any of the others … even as a fling. During that week, we also realized that we were a lot more compatible than we would have expected.

    After we got back from the cruise, we continued seeing each other because the sex was good. It was the best physical relationship I’d had in years.

    I had considered pursuing another acquaintance upon returning, but I thought I’d be sabotaging a potential relationship with that acquaintance if I started dating her while reguarly having sex with another woman. Since I’m not in a rush to get married (I don’t want kids, so there’s no urgency), I decided to wait until the fling played out.

    Within a couple weeks, I was spending 5 or 6 nights per week at her house. As a fling, she was more interested in seeing me than most of my exclusive girlfriends had been. The only exception (who saw me that often) was my most serious relationship to that point.

    Similarly, I knew the other man wasn’t treating her like his girlfriend. He’d call her once a month for a date. That guy made her feel special and desirable once per month. I made her feel special and desirable every single day.

    She was the first one to say, “I love you.” At that point, I decided that I should confirm that the other guy was no longer in the picture.

    I paid attention to the red flags. I wasn’t about to fully invest my emotions until those issues had been resolved. But I wasn’t dumping her because there was a potential problem. I waited to see if it was a genuine problem.

  24. 24

    Cool your heels a bit and give yourself (and him) some space ie don’t be so available.  If he is really interested he will pursue.  If not he will take it as an opportuinty to skip.   Keep your options open.

  25. 25

    Sorry, I’m with Gem (#10).
    In my experience, this kind of “struggling out loud” from a guy signals he’s either emotionally immature or manipulative. He’s covering his butt by voicing that he’s unsure, almost as if you’ve tricked him into liking you, while at the same time flattering you in a very low-risk way. And I’ll bet he didn’t ask you to share how you’re feeling about all of it.  Self-absorbed.
    There’s nothing wrong with him being unsure or surprised by his feelings, but to share them out loud the way you describe signals a lack of awareness and tact.
    You’re doing a great job of proceeding in a cautious, low-drama manner and taking care of yourself. There’s no need to jump ship, either. If he’ss truly interested in you, he’ll keep doing the things he’s doing right as he figures it all out. My gut feeling is that if you sit tight but continue with your life outside of him, all will be revealed & pretty quickly. If he continues to indicate that it’s all just too much for him, take him at his word, and move on. Best of luck.

  26. 26

    First, is she wife material, can she convince him to stop looking around and marry her?  Do they share hobbies and a life together in the future?  At her age, I think 3 months will be a good timeframe to determine what direction the relationship is headed in, and ask him what he thinks about the future and what he thinks about marriage in general.  Don’t rush him, but 3 months would be a decent enough time to figure out the future chances of relationship survival.

  27. 27

    I usually agree with Evan, but not this time. Mari, what he said means you’re not going to be his girlfriend anytime too soon. He’s either not looking for one, or decided you’re not going to be the one. He said that to get you to change your mind and have sex with him. He wants you to think that he is uncertain so you will rack your brains to do whatever you can to bring you guys closer so that he will want that relationship. He’s hoping that you will come up with sex. That’s what he wants from you.

    He’s a manipulator and a player. What he said to you is nothing more than a game to get sex. DUMP him now, or get hurt.

  28. 28

    “Well, last night he told me he is genuinely starting to like me, and that concerned him, because as perfect as that is, it’s not a good idea…”

    Give me a break, the above comment screams mixed messages, manipulation, RED FLAG!

    Mari, don’t play his game. Don’t even go there. Started looking around for a man that knows what he wants and has integrity. This guy ain’t it.

  29. 29

    I have read this post several times and I do agree with it.
    Simply wondering if shut him off after several months of chatting only online, when he is 10 minutes away from my work place…combined with “I am afraid that with you I could commit”,”being in love it’s not for me”,”you might be the one”, “I need to solve things with my EX”,etc..was the right decision.
    I was there…kind, funny, warm,positive, playful, hoping that he will decide to take the risk.
    He was making plans….but no actions…so I told him that I can no longer continue with this situation. After more than half a year, I believe it was the only sane choice, even if I probably lost any chance to build something normal.

  30. 30

    I say wait. 
    I had a guy that was amazing, we got along great. He was an amazing person and we started dating for 6 months, well one day he said he needed to figure things out. He needed to figure out what his career is going to look like and figure out where I fit in in his life. So I told him ok and ill be around when he figures things out. I kept in contact with him for a few months with him never really answering my text and when he did it was already way to late and I was upset so I wouldn’t text back. he would call every once in a while and we would have long nice conversations and he would never know I was upset, tell one morning I said good morning and 6 days later still no answer from him. I asked him if I did anything wrong, Of course he said he was still trying to figure out life so I let him know it was my last time texting him unless he text first I told him I loved him and I’ll be here when he figures it all out and if he finds a spot for me in his life then I would be more thin happy to be in it. Well he didn’t text back and after a few weeks i got a text from him nothing good just a hi how are you doing, I text back and we had a small conversation, but that was the start to him texting me back. I turned the tables and when he text I wouldn’t text right back this has been going on now for a few weeks and I got a ” I have been thinking about you a lot Latley and I miss you.” then tonight I got a “I wish I could wake up next to you in the morning.” 
    Hes still in proses of figuring out his life but I feel he’s trying to find a spot for me in it. Ill sit and wait no questions asked 

    1. 30.1

      Nope. Sounds like he has you as a plan B

    2. 30.2

      “Hes still in proses of figuring out his life but I feel he’s trying to find a spot for me in it. Ill sit and wait no questions asked ”

      are you serious???

    3. 30.3

      You must love him so much! Unfortunately, he is playing game with you. How heartbreaking.  The alibi – until he figures out his career and life is a classic excuse. Often times guys think they can get away with this “clever“ excuse (I am career oriented, so I must be a good and responsible guy). If he truely loves you, shouldn’t he work with you to figure out his career and a life for both of you TOGETHER NOW if he is serious about finding a lover and a life partner? Not returning your texts is ignorance (worse than being rude). DO NOT text him back and wait to see what happens next.

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