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Dear Date Advice Guy,

Two years ago I ended things with the guy I thought I was going to marry and have been trying to jump back into the dating scene ever since. However, I think I forgot how to date after being in a 3 year relationship. My friends tell me that I try to jump ahead too soon to the future and the serious things when instead I just need to sit back, keep things light, flirty, and fun for a while – to just let whatever is going to happen, happen. Thus, I end up pushing/ scaring the guy away by trying to get too serious too fast. In addition, it doesn’t help seeing all your friends happily engaged, married, or having kids; instead it turns the heat up and then I boil it over the top apparently.

So please advise women, and me, on how to keep things fun and slow in the initial stages of dating – before the relationship – and when and how to progress into the relationship stage.

Many thanks,


Dear Desperado,

Excellent question! We hear this question everywhere, don’t we? From our friends, from magazines, from movies and TV shows, and it’s always the same general idea: what is the best way to finally get serious with a guy without scaring him off?

I understand your frustration. It can be tough to get back into the dating mindset after a three-year relationship with the man who you thought was your future husband. For three years, all you knew was how to be in a relationship with that specific person. Three years later, you’re a completely different person, and all the people you meet in your single life are completely different from that one person that you’ve been accustomed to interacting with for so long. All you want is to get back to that same great situation – a loving relationship with forever in sight – but you simply don’t remember what it’s like to be single and date new people effectively. What’s a girl to do in this crazy new single life?

First of all, don’t be discouraged if you didn’t hit it off with the last few guys you’ve dated (or more, if you’re been particularly unlucky). As I’ve discussed before, finding the man who is both the type of man you’re looking for AND ready for a serious relationship is hugely dependent on random chance. The unfortunate truth is that a large percentage of men you meet in your single life simply aren’t looking (or aren’t prepared) for a serious relationship, which has nothing to do with you.

Consequently, this means that there are quite a few men out there who will date you for a while and then leave once they realize you aren’t open to a casual, mostly physical relationship. It doesn’t mean that you’re unattractive; it just means that this particular man had no interest in a serious relationship from the beginning.

But of course, there are plenty of men out there who are open to the idea of a serious relationship and are looking for their ideal lady to start a relationship with.

So how do you spot the guys who aren’t interested in serious relationships while increasing your odds of meeting the man who actually is relationship material? And how do you hit things off in the early stages of the relationship while progressing into something more long-term?

The first step is to be a fun, social person and meet as many people as possible. The more men you meet, the better the chances of one of them being the one you hit it off with. Pick up interesting hobbies. Join clubs. Go out with coworkers and meet their friends. Take classes and learn new skills or talents. Meet others who share your interests or hobbies. Chat people up.

Then, to weed out the guys who are just looking for casual flings and get the attention of the more serious men that you’re looking for, you must demonstrate that you are relationship material. You’d be surprised how quickly men can dismiss women as “not relationship material” and either dump them or just keep them around as causal flings. Another bonus here is that when you are seen as relationship material, men will be less likely to expect casual flings with you and thus less likely to pursue them.

So how do you demonstrate such quality? You must build characteristics and skills for yourself that create both types of attraction within a man. Show him that you’re a fun, interesting person while demonstrating that you’re good for him in the long run.

In addition, if you want a man to see long-term stability with you, you must demonstrate long-term stability in your own life. This means that you have long-term goals set for yourself,that you have healthy habits, that you’re disciplined and organized, and that your life is in some sort of order. If you don’t have any plans beyond what party you’re going to this weekend, you’re just ASKING for casual flings.

And finally, once you’ve hit it off with a man who you feel is ready for something serious, how do you keep things fun and avoid coming on too strongly?

First of all, it’s important not to put too much pressure on yourself by thinking about the future too much. You don’t have to plan out the next fifty years with this guy after just fifty days with him (and it’s very strange to us if you do). We can tell when you’re desperate for a serious relationship and you don’t care who it’s with. Rather, learn how to just RELAX and enjoy your time together. Remember to enjoy the JOURNEY, not simply hope to reach the destination. Honestly, the main question in your mind in the early stages should simply be “Am I having fun? Does this man make me smile?” If he can do that consistently for a few months, THEN it’s time to start thinking about something more long-term.

Here’s another tip. I am personally a big fan of the old-fashioned approach (and I’m not alone). Let him make the first moves that progress the relationship. Let him ask you out on the first date. Let him suggest that you see each other exclusively. Let him suggest meeting each other’s parents first. Let him say “I love you” first. You get the idea. Meanwhile, you just keep on being your fun, charming, put-together self. That way you keep him attracted to you, you keep having fun together, and it relieves some of the pressure from you. He gets to be the man and drive the relationship forward.

Of course, if he hesitates a bit too much to make these moves, it’s ok to drop some subtle hints that you’re ready for him to make the next move. Sometimes us guys are just a little clueless to such things (or we don’t know if you’re ready) and need a bit of a push. But remember – be patient! It can be a scary decision to move forward with a relationship.

If he still doesn’t make the next move, and there aren’t any obvious problems in the relationship, it could be that he has some secret issues, fears, or baggage that you don’t know about. Or it could be that he simply doesn’t see long-term compatibility with you and is too afraid to tell you. It happens. Hopefully you trust each other enough to openly communicate such things together and work them out as a couple. If not, and you don’t see any signs of things progressing, it may be time to move on and try again. There’s always a new guy to meet.

Keep the faith, be patient, have fun!


The Date Advice Guy

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