Tag: dating

Dating Dilemma #3: The first date

So you’ve gotten past texting and you’ve wrapped your head around the concept of talking to and even seeing more than one man at a time, but now you actually have a date. Awesome and terrifying in equal measure, simultaneously. Perfect, you are right on schedule. Meeting up for the first time should be fun and flirty, fraught with anticipation and excitement; however, more often than not it feels more like a job interview. There are questions about where to meet, (definitely a public place, don’t have anyone pick you up at your home until you feel some trust has been established); Is he going to look like his picture? Will I find him attractive? Will his voice drive me crazy? And the list is endless. I suppose it all depends whether or not you are a worrier.

Try and relax. First dates should be fun. As a general rule, men expect to pay on the first date, but if you feel strongly about it, you can go Dutch. For me first dates are practice for second dates. While awkward, try to see it as an opportunity to get out and talk to someone new. I often keep first dates short, something like coffee, a drink, or dessert; however, it really just depends on the person. I think it’s important for you to have a sense of what’s important to you on a first date and stay true to it. Here are some of my rules:

1. When possible, I like to talk on the phone before a first date. It makes me feel like I know the person better. If the phone doesn’t seem agreeable until after a meeting, I try to schedule something shorter, like coffee, in case there is no spark. I usually try to meet during the day also so that I don’t need a babysitter (Usually I can organize a playdate). If we did manage to talk on the phone, I’m more inclined to be willing to get a babysitter and go out for a full meal. Usually I let the man pick the place for a first date.

Continue reading

Dating Dilemma #2: How Many is Too Many?

So last time we talked about the importance of writing and the dilemma of remaining pen pals for too long. Remember, writing is not dating. Last time I checked, you can’t hug a computer. So let’s assume you are successful at getting past the pen pal stage, now you have the dilemma: how many men can/ should I talk to at one time? I don’t really have an answer for this because it’s different for every person, but here’s what I know: online dating is a feast or famine situation. I have never been able to talk to one person at a time. I am usually messaging more than one man and I find myself going out on casual dates with more than one person hoping that someone special breaks free from the pack.

All of this is supposed to happen naturally and it’s supposed to be fun, but somewhere along the way it feels a lot like juggling fireballs. I took juggling once for a theatre class and it wasn’t fun then, so why would I want to make it a central part of my life? I wouldn’t, but then I never anticipated that I would be partaking in the world of online dating.

Some people really do try to only talk to one person at a time, but I don’t know how they manage this, so here is what works in my world. Remember though that I have a pretty liberal moral compass. I will text and talk to several men at one time. I will go on first dates with several men without being exclusive, and I might even kiss more than one man (we’ll get into that next week when we talk about first dates), but if I decide to get physical (hey, we all have needs), I try to limit this to one person; however, sometimes even that is tricky. Hey, things happen. But this is where it gets tricky for me. I will not have a parade of men in my home, that is a personal choice because I have young children. I am fine with them knowing that I date, but I’m not okay with them knowing all that dating might entail until I actually have a boyfriend that will stick around for a while.

So that brings me back to the dilemma: How many is too many? At the moment I’m talking to seven men. I’ve met four of them, been physical with one and I’m not really sure that any of them will turn into a relationship, so I’m still on the prowl. My ultimate rule is that if I start to feel like it’s a circus then I need to slow down. I should mention that my kids are with their dad at the moment. The other thing that really works for me is I try to be honest. I don’t pretend that I’m a girlfriend if I’m not. I won’t dodge a direct question, and I function under the assumption that any man I’m seeing is also seeing other people until we have the talk. Young people seem to understand the rules of dating a little more instinctively, but for me there was a huge learning curve.

Dating in your 40’s and beyond requires all of us to make certain assumptions:

Continue reading

Dating Dilemmas #1: When did dating become about being pen pals?

This will be a series of short articles where I will share my dating dilemmas with you. I am certainly open to hearing your stories too. I will provide a private way for you to share some of the doosies and then I will incorporate them into future dating articles. This is a place where I will change names and protect your identity too. So, game on. Dating websites, look out, here comes Anne.


Honestly, what am I supposed to do with this? What if I was feeling naughty? Am I supposed to tell a complete stranger? If I was willing to engage in such conversation when I don’t even know a guy’s real name, is this the kind of person he really wants to meet anyway? And if he does, then do I want to meet him? Is he too cheap to pay for a late night phone sex session? Messages like this confuse me. I understand that engaging in online dating means that one has to type before talking. I’m not sure when the phone became intrusive and too intimate, but here we are: welcome to the world of online dating.

Some pen pal pet peeves:

1. If the culture is going to be about writing, then learn to write. Proofread people. Seriously, I find myself desperately wanting to inject grammar and spelling lessons into online profiles. I know this sounds a little harsh, but most of us have been to high school and I know for a fact that they cover the difference between to, too, and two; your and you’re; quiet and quite, and the list goes on. When in doubt, have a friend read your profile so that you’re presenting the best written version of yourself. Maybe it shouldn’t matter, or maybe it should matter more than it does, but I don’t want to miss out on Mr. Wonderful because I misspelled that I have a college degree. Apparently, there are many really smart people attending collage these days. I know because they tell me so in their profiles.

Continue reading

© 2019 Feisty Over 40

Theme by Anders NorenUp ↑