How to Get Past Her Playing HARD TO GET

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I’m a 39-year old man who has been divorced for just over a year. I’ve only dated a few women since becoming single, and am still not really comfortable with all the BS that dating seems to entail. It just seems like there is always something going on with someone you go out with that makes them less than ideal. Anyway, my question has to do with a woman who I’ve been out with six times in the past three weeks. She is also divorced, and has one teenage son. She is really pretty, and comes from a very respectable family here in town. She says she’s only dated two men in the three years that she has been divorced, and neither of them lasted more than a few months. She dresses conservatively, and does not really party too much. When I compare her to some of my friends girlfriends or wives, she is definitely a “cut above” in just about every respect so I think she would be a really good woman for me to have a long-term relationship with. The issue with her is this: she still hasn’t kissed me (or anything else). I mean we’ve given each other a hug and a peck on the last date but that was it. I would really like to make out with her and then have sex. [I’ve only had sex twice since getting divorced and those women did not last past date number 3, even though I wanted them to.] This woman just seems unapproachable and not really warm. I’d like to turn this situation around and make it more physical but I’m just not sure how to do it, and I do

not want to scare her off.  What would you suggest?


For whatever reason, she is playing hard to get with you – and from what you wrote, it sounds like that is just the way she is. Nothing wrong with that – in some cases, this is just a particular personality type. It does NOT sound like she is playing games with you – acting that way for some purpose … instead it just sounds like she is super-conservative. And my theory is reinforced by you saying she is a member of a prominent local family, and also that she dresses respectably, and does not drink excessively. She is conservative – very much so, it sounds like.

Now you – you are a relatively new midlife bachelor. You’ve been divorced for a year-ish, and are in the stage of exploring all that is out there in the dating world. You are definitely at risk of being ON THE REBOUND – which means hooking up prematurely with the wrong woman, and keeping her around too long for the wrong reasons.

MY ADVICE TO YOU RIGHT NOW in terms of jumpstarting this relationship toward something more physical is – you need to immediately take control.  Take her out to someplace romantic – and this time go for a major tongue-to-tongue kiss. The place you take her to could be a restaurant that has an outdoor view of something … or it could be a walk somewhere … the main thing is that where you go for that kiss needs to be private. In other words, don’t try to make out with her in the middle of a crowded restaurant. You get the idea. My point is – set up the situation in your mind beforehand, then just go for the major kiss. Alternatively, you could simply go for the major kiss at the conclusion of your next date – in other words, be certain she gets a great goodnight kiss.

If she reacts poorly, and pushes you away – then you will be embarrassed, so prepare yourself for that. In that case, you could either say nothing OR you could just ask her straight out why she doesn’t kiss you. If this happens, be prepared for it to be your last date – you’ve got a 50/50 probability of that happening. But if she won’t even kiss you after seven dates, then you’re just throwing good money after bad … wasting your time and hers, right?

Now when you go for that kiss, and if she kisses you back – then you need to continually push the envelope a little further until you get things where you want them. It might take another date or two – but each time push things further along. If things go well on date #7, and you get your major kiss – then I’m thinking you should be in bed with her within two more dates max. If not, then you will need to either decide that she is too much work and move on OR that you want to continue to invest your time and effort with little physical return. The motto of this website is ALWAYS GO FOR IT, and that absolutely applies to you in this case with this woman … it just means continue to push the envelope, and move things forward.

Since you are a newer midlife bachelor, I suggest you check out a number of sections of this website – which is a free resource for people just like you:

1) Rebound – Does Fear of Being Single Drive Your Behavior?
New midlife bachelors are all at high risk of exhibiting rebound behavior – so your best bet is to recognize that for what it is, and deal with it accordingly.

The next three references are part of the Midlife Dating Advice section of

2) Fundamental Truths about Women and Midlife Dating Today
A good overview of the dating landscape today from a man’s perspective.

3) Midlife Bachelor Personal Makeover
The best way to succeed as a midlife bachelor is tune up both your appearance and your attitude. Also gives you many things to watch out for – traps to avoid.

4) Develop a Strategy for Midlife Bachelor Success
This will take you through the steps necessary for you to get through your healing process, and then proactively and deliberately find the type of woman you want.

I’d also suggest that you join our Midlife Forum here – where men and women in our age group share thoughts and perspectives on dating issues much like the one you wrote in here with. Good luck – please report back with how things go. Hopefully she won’t press charges. ha ha ;o)

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.