Do You Want to Have Your Cake and Eat It, Too?

How to Open Up Your Relationship

This week, I was on the phone with a client who came to me eight weeks ago with no dating prospects whatsoever.

But armed with a new perspective on dating, online dating, and understanding men (not to mention a new online ad campaign), this woman found herself in a new position: the object of desire to a thoughtful, considerate man.

Tara, 39, went out with Ted three times. Each time, he called her in advance, made the plans, paid for her, followed up the day after, and let her know that she was a priority in his love life. Without being over-the-top smothering, Ted made it clear that he wanted to be her boyfriend.

Yet even though Tara invested a lot of money with me to ostensibly find herself a boyfriend, suddenly, when confronted with the prospect of focusing on one man, she found herself pulling away emotionally.

You know that the guy who is casually “seeing” you once a week for three months NEVER becomes your husband.

Even though he’s a great guy. Cute, smart, successful, kind.

Even though he’s done everything right.

Even though she wants to be married one day and this man is on board — Tara just couldn’t help but feel that she needed more time being single.

“More time than 39 years?” I asked.

“It’s more that I’m not sure I’m ready to commit to HIM,” she continued. “So what I’d like to do is continue to date Ted casually for the next couple of months, put my profile up on, and see what happens from there. He IS a good guy, and I don’t want to throw things away. I just want to explore my other options right now.”


Tara’s proclamation sounds eerily like the thoughts of the man who played with your heart in the past. Like your heartbreaker, she came on strong, she made a real connection, and now she’s silently backing away… sort of.

Because Tara — like your heartbreaker – doesn’t want to actually break up — she just wants to keep her distance and downgrade Ted from “future boyfriend” to “one of three men I’m seeing right now”.

Which means that, whether Tara likes it or not, Ted’s going to be on pins-and-needles, wondering where the spark and momentum went.

He’s going to be wondering what happened, what he did wrong, and how he can turn things around again.

Essentially, Tara wants to have her cake and eat it, too.

Not because she’s evil and malicious and doesn’t care about men, but because continuing to date Ted casually while exploring her other options maximizes her selfish desires.

So she gets to keep the door open for Ted, experiment with some exciting, unpredictable men on Match, and make her decision down the road.

Except that’s never how it goes.

You know that.

Because you’ve been in Ted’s position more times than you’d care to admit.

And you know that the guy who is casually “seeing” you once a week for three months NEVER becomes your husband.

How do you know this?

Because if he wanted to be your boyfriend, he’d have tried harder from the very beginning. His very indifference and ambivalence to you — shopping around for other women while keeping you in the loop — tells the entire story.

I don’t have to stick around to see the end.

Neither should Ted.

Every second you’re with the wrong guy is a second you’re not looking for the right guy.

And neither should you.

Your takeaway from this blog post should be twofold:

First, realize that men and women are no different. And although it’s easy to berate men for being selfish, for using you, for not telling you their true intentions, the real truth is: this isn’t a man thing, it’s a people thing.

I just told you Tara’s story, but I literally have THREE clients right now going through the exact same thing.

Three women with no prospects 8 weeks ago; now, all three are putting OFF having a boyfriend because they want time to date and explore and maximize.

I would probably quibble that they should consider the devoted guy instead of looking for a more exciting, unpredictable player on the Internet, but that’s neither here nor there.

All you need to know is that you have two choices: act with integrity and let your man go find a woman who’s into him, or give up on any sense of moral high ground that you might maintain when complaining about non-committal men.

You can’t have it both ways.

The second takeaway I’d like you to have is to internalize the idea that the guy who is keeping you at bay for more than 6-8 weeks is probably never going to step up to the plate to be your boyfriend.

So dump him NOW and go out and find yourself a man who is EXCITED about you.

Every second you’re with the wrong guy is a second you’re not looking for the right guy.

Join our conversation (92 Comments).
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  1. 21

    I think if she really loved this guy she wouldn’t be wanting to continue to explore other options, which is every person’s prerogative. i agree with the first comment from Johnny S, that she may want to enjoy her “power of choice”, something more often associated with men. Admittedly, my opinion is from someone a little older, with no biological clock issues and no need to marry for financial security, etc. Women should enjoy men and not feel pressure to commit just because a caring guy has come along. if nothing else, it is confidence building to date a number of different people. i agree with Evan though, that she should not string this nice man along if she doubts she would ever really be with him long tern. The important takeaway for me here, is YES, it’s great to meet a good guy who steps up to the plate, but it has to be the right one.

  2. 22

    hm… well, i’ve been on both sides, yes.
    but.   it took for me years to reilize why exactly i pull off every time i meet a good, carying guy and why i subcontiously looking for emotionally unavailable men.
    no, i’m not a heart-eater, not a player, not a man-phobiac. i love men. i really do. i admire them, their personalities and abilities which are so different from ours. but to overcome this huge, strong, life-long lasting block inside, with deeply engraved “do not trust!” – it’s hell of the deal.
    yes, it started in childhood, yes, it was fed during the early years, yes, i understand it now – but it’s just so hard to trust, even if i really, really, really want to.
    so, don’t hurry to throw the stone at such women – they suffer from that, too.

  3. 23

    EMK, you have written about clients like this one before. They spend money hiring a dating coach, then don’t take your advice, and decide they want to date around. Surprising, because you’d think that someone who goes to the trouble and expense of hiring you would be more motivated. It sounds like you have a number of clients who contact you after having recently ended long marriages. I get the sense, as SusieQ (#21) said, that they don’t have much dating experience, but then realize that they are just not ready for another serious relationship yet.

  4. 24

    Tara is being selfish. She is not acting in self-interest. She does not consider this man a “future boyfriend” and wants to “explore [her] other options”, so her plan is to use his feelings for her to keep him around while she searches for the BBD. If she were acting in her self-interest, she would end the relationship while she continues looking. She would not use him as a backup, and even if  his well-being was not her intent, it is ultimately in his best interest. I would call her a jerk and a user.

  5. 25

    I don’t think Tara is doing anything wrong. If she is now finding a lot of good men to date thanks to Evan’s coaching and good advice, it’s up to her to find the best guy  for her  if she is looking for marriage and possibly children down the track.
    Tara may be having a great time dating a few different guys and is having a lot of fun for the first time in ages.

    After 8 weeks if she wants to date other guys then she isn’t feeling it 100% for Ted. I know Evan has said if the chemistry is off the charts then run like hell, and that is very good advice if you have ever met someone who rocks your universe like never before and, yeah … where are they now!!  

    The first 8-12 weeks is sorting out whether there is some really good  things happening between you  or if there are things that are going to be  a deal breaker. You  can’t really afford to skip this step and need to take the time to get to know the other person. Everyone is on their best behaviour at first and you need to see the other person in all sorts of friends, family and social  situations.  

    If you don’t love someone and know it, let them go  to find someone who will love them.  I know it’s very hard to tell someone you don’t feel the same way but  staying with them when you don’t love them  is  pretty bad form. Better to be single for a bit longer and feel good about yourself for doing the right thing than  
    going out with someone you don’t like. Believe me, they do know and it’s a rotten feeling!  

  6. 26

    I’m interested in the time frame here. In the article Evan you state Tara went out with this man 3 times. How many hours does that translate to? 5? 10?   I believe it’s possible to know within that time frame that you want to focus on each other – opposed to dating others –   but not necessarily. Unless you were acquainted prior to dating, you barely know each other after only 3 dates. Why should one have to make a ‘commitment’ of any kind to someone they’ve spent so little time with?
    Suzie Q (Tara), you write you do love him. Do you? I will venture most of us when we love someone don’t desire to see what else might be out there because – well – we are in love. If you’ve only gone out with Ted   a few times, how can you be sure you love him? For me, it takes a couple months to develop those feelings and the result of seeing him nearly, if not every day. Many, many hours, not just a dozen or less. So I’m puzzled by how much time you and Ted have actually spent together.

  7. 27

    Kurt #15, there will be plenty of men who will want to date a 39 year old. You’ll see when you’re 39. Not everyone wants children.

    I would argue that Tara–nor anyone for that matter–doesn’t have to settle for the first good man that comes along. In fact, I would argue that clinging to the first good man that comes along when you aren’t that into him sounds desperate and fearful. It seems to me that Evan has been successful in teaching Tara how to enter the dating world, showing her that she actually has more than one prospect, and now she wants to see what that’s about. There’s nothing wrong with that and Ted is most likely not the only good man she’ll find in the process, now that she has opened herself up and has put herself out there.

    But, Tara, do Ted a favor and don’t string him along. That’s just bad taste.  

  8. 28

    @ Karl:

    I DO take responsibility for my own actions, and once I figured out that it’s OK for me to be strong and stand up and call men out for treating me like an option, then I did so.   I emailed them and said, “Thanks but no thanks.   I will not be treated like an option.   Leave me alone!”   My point is that maybe if some guys would take away from that experience, that if they don’t like how it feels to be on the receiving end of that behavior, then don’t be on the GIVING end of that behavior, either.   Just sayin.
    @ Brenda:
    YES.   Yes exactly.   I’ve been so used to being treated as an option, especially after the way my ex husband and a couple of post-divorce guys treated me, that I’m genuinely shocked by my current boyfriend’s good behavior.   I still think, “OK, I’m being punk’d.   Smile, I’m on Candid Camera!   Where’s the bad boy behavior?   Let me see it now, before we get too far and I get hurt.   I’m ready to run as soon as I see it, so let’s see it now!”   I’ve gotten so used to telling guys, sorry but you will not mistreat me, use me or abuse me, so hit the road, that it’s just ingrained.   Of course, we are all responsible for our own actions, and I had to learn the hard way, how to walk away from a guy and tell him that I won’t tolerate bad behavior.   I’m a Libra so confrontation and standing up for myself does not come easily.   I totally understand how you feel.

  9. 29

    Tara seems to be self-absorbed in the decision process of picking partner rather than focusing on the building a relationship with someone.   I’m of the opinion that a relationship is a goal to work towards and not some choice you make at the end of a month long taste test.   You are always going to cold feet if you think it’s either 1, 2 or what’s behind door number 3.

  10. 30

    “there will be plenty of men who will want to date a 39 year old. You’ll see when you’re 39. Not everyone wants children.”
    Additionally, Kurt,
    Men in that age range also *tend* to have had children already if they had a strong desire for them. Folks can contend – despite the statistics that say that people marry people within 5-7 years of themselves generally – that men in their 30s strongly prefer women in their 20s, and that a significant proportion of those women are amenable to make such preferences feasible. But you’ve got to be kidding to say that men in their 40s are in the aggregate, going to tell a woman in her 30s to jump in a lake in favor of a woman at “peak fertility,” and the same goes for any scaling up in decades. Youth is relative, there are only so many nubile college aged women to go around (actually way fewer than there used to be), and they will prefer a man who knows their favorite bands, shares their politics, and doesn’t sound like their father. 35 year olds may choose Brad Pitt over Chris Pine – possibly because they have embedded memories of him at his physical prime that they cling to – your average 20 year old woman, not so much.
    The difficulty with dating at later ages is culling. A higher and higher percentage of people who are older singles are going to be single by choice, due to chronic indecisiveness, or other personality traits that are fairly well established, difficult to modify and off-putting to many. People who are not in those categories get jaded running into folks who are and get less motivated to put themselves out there, in an increasingly fragmented social scene where people have to make an effort to find other singles over thirtysomething.
    More than likely both Ted and Tara will eventually move on. This is often going to be the natural result of being advised to date people who you feel lukewarm about until they grow on you. Sometimes they never really do, and the person is faced with the difficult choice of rejecting someone with a personal investment in you and several dates underneath their belt. Rather than reject outright, they choose to do what’s easy for them and string them along. More devious people will extract as much of an ego boost and/or as many gifts and sexual favors as they can from that person while doing so. Sometimes people that just “want a chance” shouldn’t have one for their own good, and people who are exceptionally picky need to be honest about it with their prospective partners and themselves before going forward, and step away from their vision of an ideal partner slowly by degrees, instead of entertaining people who they’d never seriously consider and wasting everyone’s time.

  11. 31

    To me, 3 dates is enough time to know that you like someone and would like to keep dating them. It is probably too soon to take down one’s dating profile and forsake all others, and definitely too soon to know whether or not you are in love. How about 3 months, rather than 3 dates? What’s the big rush, especially if you are recently divorced?
    Tara’s situation sounds different than Jackson’s (#7), who was dating a woman who was ambivalent about him for several months.

  12. 32

    This is really just a case of greener grass.   Tara has green grass, but she just can’t help wondering if there’s greener grass out there.

  13. 33

    Evan Evan Evan…..   I don’t write here, but I tweet you every so often.   Over the last 2 years of reading your blog and “Why He Disappeared”, my dating life has transformed. Right now I’m dating a guy that I wouldn’t have given the time of day before your pearls of wisdom.
    I’m compelled to write, because my really good male friend is Tara in this scenario.   He’s 41, never been married, no kids.   He’s been dating this great woman for the last 4-5 months with no progression to a relationship b/c he “likes it the way things are”.   He says he wants to be married and have kids.   I’ll be forwarding this post to him.

  14. 34

    I don’t think Tara has done anything wrong here. If she and her man have been happy with each other for three dates, that is a great and encouraging start, but not necessarily a reason to forsake all others yet. She seems to be playing it wisely. Evan, did you stop dating other women after three dates with your current wife?   It would seem that seeing how things go for at least one more month is wiser than locking in to each other now.
    Rhetorically: I’m not sure the title is appropriate to what Tara’s doing now, but what’s wrong with having your cake and eating it too? What else are you supposed to do with the cake?

  15. 35

    Jadafisk wrote:

    The difficulty with dating at later ages is culling. A higher and higher percentage of people who are older singles are going to be single by choice, due to chronic indecisiveness, or other personality traits that are fairly well established, difficult to modify and off-putting to many. People who are not in those categories get jaded running into folks who are and get less motivated to put themselves out there, in an increasingly fragmented social scene where people have to make an effort to find other singles over thirtysomething.

    Good point here.   I’ve been guilty of being pretty jaded about dating, and still am, somewhat.   Sure, we have to be responsible for our own behaviors and try to catch bad behaviors early.   But after awhile, it gets tiring, and especially if there are other things going on in your life.   For example, my Mom is battling cancer right now, so between that and the drama of dating, I would probably just take myself out of the dating pool right now, were I single.   It’s just too much, emotionally speaking.

  16. 36
    Senior Lady Vibe

    Perhaps it’s deja vu.   I recall a Ted and Tara story from last year.    

    Ted is a nice guy; following up and attending to Tara is a good indication of that.   But what  happens when —   due to a sudden online dating “feast” — there are three first dates in a week, all nice guys, all following up?   Eight or nine hours into a relationship is still too soon for instant devotion from any of the men.   I’d be comfortable with getting to know them over a longer period of time.

    I like cake.   Not enough to make me sick but I’d  appreciate a  creamy-frosted  slice or two…    

    BTW, women the age of Alyssa Milano and Jennifer Garner seem young to me… but then again, I’m ancient.   Are they really being culled out due to  advanced age?    Really?


  17. 37

    Sephor @23, I would agree  IF she doesn’t tell this man her state of mine and let him go so he can do what’s right for him. It’s all about honesty and ethics. When a person starts putting their own self interests above hurting someone, then they are bad news.

  18. 38

    Margo #39: I would agree IF she doesn’t tell this man her state of mine…

    Will she tell him? If she tells him, what will she tell him? Will she tell him that she does not see him as her boyfriend. but that she does think that he’s good enough (for now)  to take her on dates? Will she tell him that she doesn’t “want to throw things away” with him, but there might be someone out there better than him, so does he mind waiting while she finds out? Will she tell him that he is only  “one of the three men [she’s] seeing right now”?

    She knows he wants to be her boyfriend, and she knows that she does not want to be his girlfriend. If she stops seeing him, she can concentrate on finding the man for whom she does want to be a girlfriend.

  19. 39

    I tend to agree on Johnny S on @1. It is a tricky road, thought, because should Ted suddenly turn around and cut it all off, she will be feeling not so secure exploring other options. Having said that, if she does not feeling it for Ted, she would not still be happy being with him. Honest would be probably to say it to him, how things are.

  20. 40

    I respectfully disagree with Evan. This is NOT a “people” thing but a gender thing. Men don’t keep women around as “options”. They keep women around as booty calls – women they find attractive enough to want to sleep with, but not have long term meaningful relationships with. Thankfully they are not the majority of men, though a significant minority. Women, on the other hand, are opposite. They keep men around as truly “options”. Men they think they could have meaningful relationships with, but whom they are not madly deeply crazily attracted to, physically and sexually.   They want to have these men to fall back upon should things not work out (which they never usually do) with their hotter, more exciting prospects. Unlike player men, there are many many many women out there who are like this. This is not to say they are bad women, but they just normal women exhibiting normal self interested behavior.

    1. 40.1

      ….and this gives you the right to use them…wow…this is the mindset many women have nowadays and it is indeed disgusting and selfish imo. *smh*

      1. 40.1.1

        @ nyne # 40.1
        “wow…this is the mindset many women have nowadays and it is indeed disgusting and selfish imo”
        Are you being ironic/sarcastic? If not, then I strongly disagree — I think women are fully entitled to exercise all their available ”options” in order to strike their best deal. Until a guy asks a woman for commitment she is fully entitled to continue to assess any available options she has. And men know this. However, many men like to be able to consider their options whilst secretly hoping the woman isn’t doing the same: I’m sorry, but it doesn’t work like that.
          Maybe you need to up your game nyne, instead of complaining about women playing theirs.
        @ Androgynous #40
        “This is not to say they are bad women, but they just normal women exhibiting normal self interested behavior”
        I agree.
        Good comment and analysis of how dating works btw.

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