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:

1. We all have baggage. Everyone you meet has a past that they are trying to work through and that happens for each of us in our own way and in our own time. While men and women may deal with baggage differently, we all have to deal with it.

2. People are at different stages of the dating process. Don’t be naïve, dating is a process. Someone who is separated may be looking for something different than someone that has been single for a long time. People may truly believe that they are ready for a relationship and then realize that they are not after they have sex with you. You just never know.

3. You need to protect yourself. You need to be as safe as possible. Use a condom when you’re with someone new. If he refuses, get him away from you. While condoms can’t protect against everything, it’s a good start. Most men know that’s part of the deal. It might be a good idea to look into the vaccination for HPV because over 80% of the population has the virus, so it might be wise to try and protect yourself from the most dangerous strands. I know, not the most pleasant conversation, but it’s important to respect yourself and the people that you choose to be with.

4. Try to have fun. While the ultimate goal may be to get married again, you can’t start there. You need to start at the beginning. Try and see the beginning as a fun do over (yeah, I know it’s not always fun), but the less worried you are, the more fun dating can be. You don’t have to have a relationship with a guy just because you slept with him. Believe me, he had fun. You don’t have to settle for things that drive you crazy. If it’s annoying after a few dates, add 10 years and just imagine. It’s okay to cut your losses and move on. It’s also okay to try and enjoy the people that you meet. There are some decent guys out there and they are just as confused as you are. In my experience, they are happy to talk about it.

5. Be honest, at least with yourself. You don’t need to let every guy that you have coffee with know your whole life story, but It’s okay to practice talking and dating, and even kissing. You just need to be honest with yourself. If you know that you want sex, then be prepared for that, if you know you want a relationship then you might apply different criteria. You don’t need to tell your date everything (if I have a motive, I generally tell them, but that’s just me), but be honest with yourself about what you’re doing. This is often easier said than done.

I wish I could tell you that once you move past the incessant texting stage that you’re home free, but that just isn’t how this works. In fact, it seems to be confusing from start to finish. I’m trying to embrace that, but I get impatient. I make mistakes. I say too much, or not enough. It is not a perfect science with a rulebook. I tried reading countless articles about what men want, and how to be desirable, and coy, and I have found all of that to be less than helpful. I really think that being yourself, warts and all, is the best way to approach online dating. I try to figure out what my rules are and follow them so that I don’t get unnecessarily hurt. That doesn’t mean that everything I want is rated PG or that I would want to tell my mom, but I am able to look at myself in the mirror every day, so, so far, so good. Best of luck out there.

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