Second Date Dilemma

by Tamar Caspi under Date Night,Relationships

Dear Tamar,

I met a new guy on Tuesday night and we liked one another…he asked me out for the following night, but I was busy so we scheduled a date for Saturday night. It’s Friday now and I haven’t heard from him. He had said we were getting together for sure on Saturday night so my question is, since he hasn’t called yet to make firm plans, should I call him or wait till he calls me? Thanks in advance.

Dear Second Date Dilemma,

As women we’re taught to believe that if we call a guy he’ll think we’re overly-aggressive and will scare him off. But, I say you have nothing to lose except plans with someone else on Saturday night. Go ahead and call him.  Be upbeat and cheerful and simply ask him casually if you are still on for tomorrow — but don’t turn it into a long conversation and don’t tell him you were nervous he was going to stand you up. If he doesn’t answer leave a message with the same question using a positive tone of voice. Chances are (I hope) that he felt the plans were concrete so he was going to wait until Saturday to discuss where to meet, etc. Guys can be a little dense like that and sometimes fail to realize that we ladies like to primp and prep, especially for a Saturday night — prime night — date. If he says no or doesn’t answer and doesn’t call you back, well that sucks, plain and simple. Hopefully he’ll call to apologize at which point you can decide if you want to give him a second chance, or he’s just a dud and you’ll remember that one awesome date, but I bet he just hadn’t gotten around to calling yet and that you will have an awesome date  tomorrow! Good luck!


Ready to Give Up

by Tamar Caspi under Date Night,JDate,Relationships,Single Life

Dear Tamar,

I am so incredibly puzzled. I have gone on numerous dates that all seem really great. They’d last an average of 2-3 hours for dinner. My photos are completely accurate and updated.  In fact, I am often thanked for being so honest. I am 48 and look much younger (and awkward to say about myself, but I am considered very attractive). I have teens and am dating men around the same age as me. I have been completely puzzled because I am not being called for second dates by those I would like to have a second date with. One recently texted 30 minutes after the date to say he had a great time…and then no follow up. I am really confused and feel like shelving dating.

Dear Ready to Give Up,

Don’t shelf dating just yet. I look at this from a “so far, so good” perspective: you obviously have good photos (and look like them!), you have a lot of life left to live and the men are spending a pretty big chunk of their time with you. If you remember dating the first time around, you’ll recall it wasn’t easy then either. And now you’re bringing age, experience, kids, and all the pluses and minuses that come with that to the table — and probably so are the men you’re dating. So what’s the problem? Why aren’t you getting 2nd dates?

I think what you have to look at are the conversations you’re having on the dates: are you talking about yourself and asking questions about your date? Or, are you commiserating about your past relationships, the stress of having teenagers and so forth? Although these topics may seem like bonding conversations and you may think that by putting all your cards on the table the man will know what he’s getting into, these topics also have negative connotations and may not leave a man thinking he’s had a great time.  Instead, he may think he’s left a therapy session.

Once you meet someone you like you’ll each have plenty of time to discuss your past, but right now you should be talking about upbeat, positive subjects. What interests and hobbies do you have in common? Play Jewish Geography (but don’t talk badly about anyone, that’s bad karma). Talk about what you’re both looking for in the future. I believe if you stick to these topics on 1st dates you will start landing some 2nd dates. Just don’t give up, it will happen! Good luck!