Dating Advice: Call Too Often I’m a Stalker, Don’t Call Enough I’m a Jerk


dating advice




Said to me by a single guy in his early fifties seeking dating advice:


“I have a great topic for you to write about. As a guy, one of my biggest issues in dating is that these women are impossible to please. If I call too often I’m a stalker, and if I don’t call enough, I’m a jerk. It’s like they don’t know what they want.”


I think my friend is right, that this is a tough dating issue. It also goes both ways, meaning men feel the same regarding women reaching out to them. A woman who calls or texts frequently is a turnoff in some cases, and a woman who doesn’t reach out often could come off as distant, cold or just not interested.




You’d think in dating at an older age—after divorce, with kids, etc., the games would stop (or at least slow down) and people would just be themselves and show their authentic feelings. But there’s a reason so many people don’t or just can’t: baggage.


By this age, let’s assume most people have been in serious relationships and have had their heart broken at least once. So, we all come with heavy baggage that makes us extra careful, insecure at times and often borderline paranoid. It’s hard to trust again, both yourself (your judgment) and the people you are dating. So everyone has their guard up much more so than we did in our twenties, and with that guard comes the games.


I’ll wait a couple days to call her so she doesn’t think I’m desperate or too interested. I’m not going to take my profile off Match until I see that he has. Sound familiar? It’s sad, but for those who have been wronged a few times, it’s the way they think they are staying in control, which is kind of a joke because playing games is a sign you of the exact opposite—meaning you have no control.



So, let me try to answer my friend’s dilemma by offering dating advice in regards to “how often should I call (or text?)” Obviously there are no rules (or that would be game playing) so I can only offer what I think makes sense:

     1. It depends on the person. What I have found in dating is, it’s usually black and white, meaning there is either a connection or there isn’t. In a few cases, I can remember thinking, ‘I’ll go out with him one more time because I’m not sure,’ but the majority of the time, you know instantly. I’m even going to say you know in the first 15 minutes of the date. So, if I go on a date with a guy and I really like him, there’s no such thing as too much texting or calling. Bring on the stalking! What that means is, if a woman is calling a guy a stalker (in a negative way), then she doesn’t want to hear from him because—to quote the book and movie, “He’s Just Not That Into You,” “She’s just not that into you.”

    2. Timing matters. Maybe the girl just got out of a long relationship or isn’t really ready to date after her divorce. Timing really has a lot to do with love, in my opinion. So, if you call or text too much, it might scare her, but if you call too little, she might lose trust in you and think you are unreliable, playing games, dating lots of other women, or that you just don’t care about her that much. It’s tricky.

     3. Be your authentic self. If you want to text or call, just do it. Remember, if he or she really likes you, they will be happy to hear from you. If they don’t, they won’t, and that’s OK. It just means the connection wasn’t there or the timing was bad. And if you don’t text or call because you are afraid you are going to scare the person off, it isn’t going to make a difference. They are going to dump you anyhow. Now, I do have to say that it is wise to hold back just a little bit at the beginning, because if you bombard someone really early on, that could be off-putting. But I’m talking about the first few weeks. After that, it has to be real and authentic. And if the person doesn’t like it, you have to accept it, try not to take it too personally and move on.

Dating really isn’t easy. Sometimes you have to go through a string of bad relationships to find a really, really good one. Patience is key, but even more so is being yourself. No one can take that away from you.


And when you meet someone and it clicks like crazy, when that happens, dating couldn’t be easier. Everything goes on autopilot and the two of you start to fly! Kind of makes all the bad dates and the people who hurt you worth it. And someday, with that right person, it won’t matter how often or how little you call. It will be right.


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Guy Grinning is a blog for men facing divorce and dating after divorce. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues.

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