To play games or not?

Deb writes:

“I have had 4 dates with one man and I find him very interesting, funny, smart and a gentleman. How do I tell if he is really interested in me? I have read books and everything says to play a game, acting like you are not interested and he will come after you. I want an honest, open and upfront relationship. Do I tell him that I like him and flat out ask if he feels the same. Or do I go with the game of acting like I am not interested?”

Ah, Deb. The age-old question of, “Do I turn him off if I show I’m interested, or pretend to be aloof and coy in the hopes of enticing him?”

This conundrum has plagued women for decades (nay, centuries?).

First, I’m never for playing games. I, like you, prefer to be straightforward. That said, timing and word choice are everything. If you ask “Are you interested in me long term?” in the first few dates, you’ll sound needy and inappropriate.

I think the key is not what is *said* but what is done. Even if he answered, “Yes, I’m interested in you long term” then did little to show his interest, his actions (or inactions) create confusion and frustration, but really show his interest level. So it’s almost a moot point what you ask or what he says. You look for the actions that show he cares.

Caveat: In “Signs of endearment — or just habits?” I discuss how I misinterpreted what I thought were signs of caring, when really they were just my then-beaus habits around any woman. So actions nor words on their own are beacons into his thoughts and heart.

So my advice is to continue to show interest in him, accept his invitations, smile and laugh, but go slow. Look for the signs that says he’s interested in you beyond a quick fling. His introducing you to his friends and family is a solid sign, but it’s not the only thing to look for.

In other words, don’t broach the “Do you like me?” conversation. Keep it light and fun. When he brings it up, it will be more likely he wants to get more serious.

Readers, what do you think about Deb’s situation?
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15 responses to “To play games or not?”

  1. Mark Avatar

    Don’t play games. Be genuine. Flirting is ok. Game playing isn’t.

    I think that rather than asking if he’s interested in her, what Deb’s really wanting to know is if he looks at her as a possible long-term partner.

    Clearly, he’s interested. You don’t have four dates if you’re not interested.

    The long-term thing is more difficult, though. Some people, man or woman, want a long-term live-in relationship. Others don’t. Others may want a long-term dating relationship but don’t want to give up their independence.

    It’s too early to start asking those questions. Is Deb turning down other dates or social engagements with friends to spend time with this new man? If not, why even worry at this point?

  2. katie Avatar

    It sounds like the “either tell him how I feel and ask him how he feels” and the “play coy” are simply two points on a long continuum of possibilities. Deb might feel far less stuck if she sat down and made a list of a half dozen more points on that continuum, looked at them, found one or two that feel like a good fit, and journeyed patiently in that direction.

    The phrase “playing games” triggers a lot of unpleasant connotations — like deception, dishonesty, manipulation, etc. Perhaps a different perspective is that in the early stages of a relationship each person is holding their cards close to their chest, watching and waiting before saying too much or professing feelings before their time. There is not game playing; it is wisdom.

  3. Rosemary Breen| Avatar
    Rosemary Breen|

    Yeah! There is no need to play around. For heaven sakes you have had 4 dates and it these were genuine dates then i’d say all the right lights are flashing.
    Is this more a question of personal confidence perhaps?

  4. Ronnie Ann Ryan - The Dating Coach Avatar

    The Dating Goddess made some good points. And I often use the same analogy with my over 40 dating coaching clients that Katie has here – its like playing poker – you hold your cards close to the vest so you don’t reveal your hand.

    Women often want to be “honest and direct” and think anything else is game playing. But that is not true. The point here is some things, you have to wait and see. Dating is one of those thing and only time will tell.

    I don’t even agree that four dates with the same guy means he’s seriously interested. On my dating journey to meet my husband, I dated a guy four times and then got a “Dear John” letter from him..

    Dating is like high school chemistry – you put all the ingredients into the glass beaker, stir, turn on then flame and then stand back to observe. Same goes for dating.

    You watch to discover – do you enjoy his sense of humor and the same activities? Does he treat you right, call often, ask about your day and really listen? Do you agree with his code of ethicsa nd have a similar away of looking at the world? Do you have fun together? Does he try to find out what you like, please you and introduce you to his family and friends as his girlfriend?

    Observation is the only way to know how he thinks of you during the initial dating phase, until he brings it up – as the Dating Goddess pointed out. So, as I tell my over 40 dating coaching clients, take a deep breath, feel free to date others until he asks for exclusivity and do your best to simply enjoy the ride.

  5. Richard Avatar

    I presume we are all over 40. If you ask and scare him off, then what have you scared off? An over 40 guy scared of commitment. So, what have you lost? He is not a 20 year old that doesn’t know what he wants out of life, and you are trying to coax him into a life of domesticity. If he is a confirmed bachelor, then better to know that sooner rather than later and move on to the next guy. If he is emotionally damaged from his prior relationship, then better to let him find you when he is fixed.

    The question to ask is not “are you the one for him”, but “does he see potential in the relationship, and is he the marrying type”. After four dates, you are interested in the guy, and you are wondering what are his intentions. Fair enough.

    So, what are the other possible outcomes of asking:
    1) He is scared off. Assuming you do not ask in a needy way, I can’t think of a scenario where it is bad to scare him off.
    2) He likes you too and would like to continue dating towards the possibility of a LTR.
    3) He doesn’t know. Fair enough. At least you know you are still in the exploring stage.
    4) He likes you (tolerates you) and just wants to have a buddy (or more) until he finds a new playmate.
    5) He is #4 but pretends he is #2 or #3. This is what you have to be careful about and make sure his actions match his words.

    I say be open and honest. That is where you want to end up anyway. Might as well start there. You may need to “trust but verify” with someone who has not yet earned your trust.

    Exception: He is such a great catch that you are willing to invest the time and effort needed to coax an over 40 confirmed bachelor into a life of domesticity. You will not have been the first to try, so you better be great at playing the game. You should already be planning 5 steps ahead, and not struggling with a beginning step.

    Now, if you want to play games to make sure he is worthy of you, that is a totally different question.

  6. Karen Avatar

    I also agree that 4 dates isn’t evidence at all that he’s totally “into” you and wants to marry you etc.

    In fact, 4 dates is about how long I normally date any guy I just met who isn’t totally offensive. Giving a guy the benefit of the doubt for 4 dates gives us both time to stop being nervous, and maybe explore if some physical chemistry is “there”. But after 4 dates and I’m bored or there’s nothing much to talk about, I feel confident that I’m not jumping to conclusions when I tell him it’s not a match.

    I agree that you can’t scare off a man who is “into” you by coming on strong sexually. I have found that most men are happy to match your sexual interest even if they aren’t interested in commitment! On the other hand, asking for marriage intent/commitment after only 4 dates is highly likely to scare off 100% of sane men. If a man asked me whether I wanted to marry him after only 4 dates, I’d flee myself!

    Honestly, you are dating. Enjoy the process of getting to know each other! During 2-3 months of dating you should have had some conversations naturally about each others’ lives, your goals for relationships in general–looking to get married ever in the future or not, looking for a LTR in general, whether exclusivity is important to either of you if you decide to make the relationship a sexual one, etc.

    Yes your answers to questions during this time may make him decide to end it with you. And vice versa. Why is this bad or to be avoided? You need to know if you’re compatible–if you’re not compatible, why would you want to stay together anyway–you’d just be miserable!

  7. julie Avatar

    On the flip side, I’ve been very turned off by men who seem to be only into dating me so that can fill a void and be involved in a relationship. It seems less about who I am as a person when I hear this quickly and more about the person being lonely and insecure.

    Don’t get me wrong, I’ve rushed things along when I’ve felt excited and into a man, but I wish to my core I had just let things progress naturally instead of focusing on the future so much.

  8. Darren Miller Avatar

    ve played games and I have been straight up and in my opinion, you need a middle ground. Dating Goddess has made an important point to make sure you do not get too attached to the person before you know the score.

    If you are still unclear, it is time to judge with actions, as Dating Goddess ‘actions speak louder than words’. A guy will never tell you how he feels about you at the beginning of a relationship.

    However, it is a good sign if he is interested in what you’re doing within your life, whether it’s work or hobbies etc. If he asks you what you want to do or where you want to go, you can tell your happiness is important to him. You already mentioned he has been spending time with you, my question would be ‘has it been consistent?’ Whatever he says hes going to do, does he do it?

    Rosemary Breen is right you cannot base anything on 4 dates. No way! Statistics say that before weighing up whether he is relationship material you need to go on at least 9 dates.

    In my opinion times have changed so I wouldn’t go by that at all. All I would say is enjoy dating and wait until you feel the time is right to approach the subject as to whether it is time for the relationship to move forward.

  9. Mitsy Avatar

    “In fact, 4 dates is about how long I normally date any guy I just met who isn’t totally offensive.”

    LOL I love how Karen puts this.

    I also agree w/many of the other posts. Some really good advice/insight by everyone. I, too, have gone out with guys who seemed to be looking to fill a void (and not so much as to get to know me). Likewise, I’ve also felt needy & probably said the wrong things as well. But, like another poster mentioned, if a guy (over 40) is too easily scared off, then he ISN’T the right one.

    I think there’s a fine line between game playing, being totally honest and having the wisdom to realize that if you have to WORK way too hard to win someone over, they just might not be the right person. You don’t have to completely make yourself over or try to always say & do everything perfect in order to find the right match. Because eventually, we all have to be our authentic selves. Quite a few times (with online dating), I found that a guy would woo me and seem like such a great guy until he realized he had me and thus, quit making much effort later. Took me a while to realize that they are not the right one either if they take that approach.

    You really just have to live & learn. There is no one particular formula for success. Wish there was. 🙁

  10. Robert Avatar

    Don’t play games. We are adults here.

    I think the underlying question is should I have sex with him (to be blunt). I don’t think there are any hard and fast rules.

    The first question is how important is making love to you? After 4 dates it is not a one night stand. There is some connection. How would you feel if you made love to him several times and then it did not work out? If it would harm you, then take things slow. But realise that after 6 or so dates he may give up on you. I suspect I would. If there was really something there, things would be hot and heavy by this time.

    The second question is what is the relationship like. If on the 4th date you are still getting to know each other, then I would take things slow. But I would definitely let him know you are interested and excited. Deep kisses would do that I think. On the other hand if you are comfortable with meaningful love making without a long term commitment (see #1 above), you are making a real connection and the relationship is hot and heavy, then I would say go for it. You are both adults and can take responsibility for what you are doing. Sex is fun and fulfilling. It is not a casual one night stand but a sharing of a meaningful connection (making love). If it only lasts for a couple of months, it still is a satisfying relationship. We are adults and making love fulfills an important part of who we are. It is OK if it does not lead to a long term relationship.

    I think women many times set to high a standard; “It has to be a long term relationship.” So they either deny themselves any sex and are furstrated. Or fall into a one night stand because they have a real need be fulfilled. I think both are worse than real intimacy that only lasts a few months. But these are only my thoughts and I am a guy…

    What is the quote?
    “It is better to have loved and lost than never to have loved at all”

    One caution, make sure he is not married or in another relationship. Do some checking. There are cads out there.

  11. Mitsy Avatar

    Robert’s thinking is probably what a majority of men think about sex and let’s put it this way, if sex is someone’s main goal, you’re always going to be able to find someone to do that with. Guys are probably better at doing casual sex than women are. If a guy would expect sex after “6” dates with me and give up after that, then he was NOT the guy for me. I’m going to guess I’m not in the minority in my thinking here.

    And if you’ve been burned more than a few times (like many women 40 & over), the payoff for jumping in the sack too early is short lived at best if you really don’t think it’s going to be long-term. There is no guarantee for sure, but if you go with the theory that you have missed out on all the great sex that’s out there, then you’re also setting yourself up for heartache if you’re actually looking for a long-term relationship. I know that I’m not wired to have casual sex. If I’m having sex with a guy, it’s because we’re in a long-term relationship and I expect and hope for it to continue. A guy who has a similar thought process is the key and a few guys seem to know what to say in order to get what they want and those are the types I encountered online. Thankfully, I only got involved with 1 guy physically way too soon. The others I soon realized were not serious about anything long-term.

  12. Kas Thomas Avatar

    You’re really trying to find out two things: Is he looking for a long-term relationship (in general), and secondly, is he looking at YOU that way. I think if he’s looking for a LTR, then the answer to the second question will be self-evident after a while and you should just let the answer develop naturally. But it’s fair to want to know from someone, up front, what they are looking for at this point in their dating life. What you can do is either asking him directly (but making it a general question — not about you specifically), or ask him indirectly: Ask him if he is registered with any dating sites, and if so, what did he put when filling out the portion of his profile devoted to dating goals. If he put “friends and activity partners,” that’s one thing. (If he put “casual sex,” good luck.) Hopefully he put “short- and long-term dating” or looking for a life partner, or whatever. If he is not registered with a dating site, ask him point-blank what he WOULD put in his profile if he WERE registered with a dating site.

    In summary: First find out if he’s serious in general. Then find out if he’s serious about you. The latter, you should only ask directly if there’s a crisis brewing. Don’t create a crisis unnecessarily by asking it too directly too soon.


  13. Karen Avatar

    I’m 60, the fellow I’ve been dating is 61. we’re gone out now for 12 weeks….some times more than once a week. It took till the 4th date before I received a good night kiss (and I had to instigate it!). I really enjoy his company, we have a LOT of similar interests and values. I’m looking for a long term dating relationship but an ALSO looking for physical intimacy as well….to me that is important. Everytime I kiss him passionately, or make it known that I’m interested in becoming closer, he pulls back! He still asks me out again…..but now I’m CONFUSED!

    WHAT THE HECK is going on! Is he turned off by me? If so, why is he still asking me out….It he so “religious” that he’s trying NOT to “sin” (yeah, right…..I’m not in the habit of buying ocean front property in Denver!). Does he have a physical problem? Heck I’m a nurse and that can be managed. Do I ask, or do I wait!

  14. Shawn Avatar

    Well, by playing games you will end up no where. You need to be honest in a relationship right from the get go.

  15. Janett Brown Avatar

    I think you have to be yourself. Don’t do things just to please him because this means that you are going to wear a mask and one day you won’t be able to wear it anymore. And if he really loves you, he will love for what you are.