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Section 19: Multi-Dating

I'm fairly adamant that multi-dating doesn't work in any way, shape or form for someone looking for a long-term relationship. There are exceptions, but I'm going to argue that no good can come specifically from multi-dating.

What is multi-dating? I wouldn't consider arranging overlapping first dates to be multi-dating. If you like someone enough you've dated to consider additional dating, then multi-dating is any romantic discussion or activity with anyone else.

This is not a commitment to this person you're dating. He or she could have absolutely no idea that you're restricting other contact. This is solely for you, so that you can focus your attention on the concept of whether this person is a potential long-term partner.

If you determine that this isn't a potential exclusive relationship, you don't owe that person any explanation or loyalty. You can move right back into other contacts without violating the concept of not multi-dating.

I've heard the argument that multi-dating keeps some people from investing too much in a relationship too soon. I don't understand how this is relevant. If you lack the skills to properly evaluate a relationship, then how is adding more relationships to the mix going to make anything any clearer? You're still out on dates that could turn into something more. On the other side of the equation, your prospective partner is dating someone who is consciously thinking about and evaluating someone else. How is this any different than someone hung up on an ex?

When you multi-date, you add to the complexity of the situation by setting up, consciously or unconsciously, a competition between those you are dating. Winning that competition is often more a chemistry race than it is a true evaluation.

You also have to be careful to keep multi-dating secret. If you let your partners know there's competition, those who don't like multi-dating will drop out if they have any self respect. And those who don't may simply like the idea of winning. Once they've won, you then have the added risk that they might momentarily enjoy the euphoria of a challenge conquered, and may want to move on to the next challenge.

Another popular argument is that you should multi-date because you can't know or stop your dating contacts from multi-dating themselves. So you protect yourself by assuming they, too, are multi-dating.

I don't understand the logic there. First of all, your dating behavior should reflect your goals, not the expected behavior of people you don't even know. On the surface, "he's probably doing it, so you should, too" sounds like good advice. But it doesn't hold up to any kind of rational analysis. Why should he control your activity?

Let's say you aren't multi-dating and he is, where are you, exactly? He's probably not in the group who will care if you're multi-dating, so there's no risk that you will turn him off if you start (and if you do turn him off, you've exposed a hypocrite, so there's that in your favor). But what you've done is set up a competition for your attention. Now you're no longer dating to learn about someone, you're dating until someone demands exclusivity or until you demand exclusivity. You've added a layer of complexity to this equation by adding new contacts to the mix. This only benefits you if you prefer multi-dating anyway.

What do you lose, if you don't like multi-dating, by using this logic? You've allowed the real or imaginary behavior of your contacts to change your behavior. And, if it turns out that he isn't actually multi-dating, you've added the risk that he will be turned off by your dating behavior.

So, however you feel about multi-dating, it makes absolutely no sense to do it simply because you can't control whether your prospective partners are multi-dating.

We should value ourselves. While commitment is a natural goal for those of us who prefer exclusive relationships, trying to move forward with someone who is multi-dating is often quite difficult. Because it's a competition, we may call and try and set up a date for the weekend and find that person "busy with work" or some other excuse (multi-dating does lead itself naturally to white lies to protect our feelings, which may or may not be deal-breakers). We may wait a couple of weeks for even the most casual contact because that person is busy giving a closer evaluation to choice 1-A. That happens with multi-dating, and you may be fine with it. The question, then, is at what point do you demand exclusivity for your attention? At what point do you care if you get knocked back to 1-B or even 1-C and you don't get those prime weekend dating spots any more?

If you feel that point could ever exist, what benefit do you obtain from putting up with multi-dating in the first place? The only way you win this game is if both of you are always 1-A.

Why do we date? Yes, it's fun to meet new people and it's certainly fun to make a new connection. There are many out there who don't want commitment and enjoy dating. There's nothing wrong with that. I'm certainly not going to make any argument encouraging complete celibacy unless you're in a committed relationship. That's a decision that can go either way, as long as people are honest about it.

But if you're dating to find a lasting relationship, multi-dating only complicates the process and adds unnecessary barriers to success. The only gains I see from multi-dating are for those of us who can't stand being alone and those who constantly need to feed their egos by not letting themselves get into a situation where they care more about someone else than that person cares about them. The solution for this problem is to gain confidence in yourself and stop caring so much about protecting your own ego.

Section 20: Friends with Benefits

We hear the term "friends with benefits" a lot. It's a label that has many different meanings. It's often used to project a maturity onto something that doesn't require maturity. It's more an extreme case of pretending your emotions are irrelevant when it comes to having a relationship.

People use this term to convey a relationship where sex is expected and there's no commitment. Some say this is an exclusive relationship, but it can end at any time. Some say you don't do things as friends - meeting is just for sex. Others say it can be a regular friendship with occasional trips to the bedroom.

But it is just a label, and, no matter how hard you try to define it, each partner will have a different view of the relationship.

I prefer to look at relationships as a series of sliders. What is the level of commitment? What is the level of exclusivity? What role does sex play? What role does communication play? These are all sliders that define a relationship. And these sliders can move at any time. I guarantee you that anyone who thinks he or she is in a friends with benefits arrangement has a different view of these sliders than his or her partner.

Can this type of arrangement turn into a "regular" relationship? Yes, because it is a relationship. You can define it any way you want. You can communicate a desire to change it any time you want. This carries risk, but life is filled with risks. Will it definitely become a more committed relationship if you ask? No. You might well find that your idea of where the commitment slider resides and where it can move is very different from your partner's definition.

If you're consciously hiding your emotional connection because your partner wants friends with benefits and you may not, that's probably a recipe for significant pain at some time down the road.

Communication is the key to this type of casual relationship, and having that type of communication seems to violate the fundamental assumption of friends with benefits. I can't say it's impossible to make this work. It isn't. But it does require a lot of specific understanding to avoid a situation where the two different views of the relationship are so far apart that the pain is inevitable once one partner starts to feel differently about the other.

Section 21: Contact Frequency

This is one of those areas where men and women are different, even though they have the same feelings coursing through their veins.

Are there rules here? Not really. But contact compatibility is a vital part of any relationship. If two people are in a committed relationship and otherwise behaving well, if there's significant frustration over contact, that's a serious, but fixable, problem.

Generally, men make the first move. On dating sites, it's perfectly OK for the woman to message first. Either way, messages should be real messages, not winks or nudges or bumps or "hi there" or other semi-sentient sentiment.

If the initial meet was off-line, and the man has your number, you can assume he wasn't interested if he waits more than a week to use it. After a week, he's either in another relationship, was never interested in the first place, lost your number, got into an accident or is in jail.

Once communication begins, it's good to respond to each message within about 24 hours. Shorter delays are fine, but no shorter than an hour or two initially. Try and match the length and intensity of the last message you received. That will give this person the impression you're in synch. I tried to go one paragraph longer if I felt good about the contact. The idea behind that was to let the other person know that I was willing to put myself out there and let her increase the message intensity if she was comfortable.

Some people are more comfortable than others with longer messages early on. The important thing is to find someone who is still contributing to the conversation and that conversation is still moving forward, even if it's only moving forward slowly.

Within a few messages, once you've established that conversations can move forward, it's usually time to meet. Again, the man should suggest meeting. He should choose something casual and a place with a well-lit parking lot (or close to a metro station) where both can arrive comfortable and safely.

If I ever found myself in that place where messaging had gone on a couple of weeks and I still hadn't suggested meeting, it was solely because the conversation really wasn't moving forward or working. I was impressed with the pictures and/or the profile, but felt like she wasn't putting anything into the equation. I never did meet any of those drawn-out initial contacts.

After meeting, contact is more a question of personal preference. Some people (like me) absolutely despise text messages. I've gone as far as to turn off text messaging on my phone. Some people (like me) don't want phone calls or messages at work. And some people (unlike me) need to be in frequent contact with their partners throughout the day. This can cause serious conflicts. Just keep in mind that you can feel very strongly about a person, yet hate the idea of constant text bantering.

At the same time, you have to remember the "he's not that into you" mantra. This can be a tough line to navigate. If someone just isn't communicating at all, or greatly changes his or her pattern of communication depending on seemingly random factors, it could well be a sign that there's no real interest in a relationship or maybe there's another person involved.

Early on, it's not cool to force communication. Frequent messages wondering why there's no response could well be seen as a deal-breaker. Trying to force someone to change his or her contact style could also be a deal-breaker.

Ladies, if you had a first date and don't hear back within a few days, just let it go. A polite "I had a great time" right after the date is great. But it is up to him to contact you for a second date unless expressly negotiated beforehand. If he doesn't, following up repeatedly will actually hurt your chances more than it will help your chances. Above all, resist the temptation to send an angry "you're a jerk for turning me down" email or text. The only potential benefit of that message is to massage your own ego, and, in reality, it's only going to massage his ego.

Just be respectful and you'll probably be all right. When in doubt, look at the entire history of contact with this person to try and determine if there's a new problem.

Section 22: Knowing when to let go

Dating the wrong person can become far more than an ego bruise. When you know it's not going well and you don't think things are going to improve, you have to let go of the relationship.

That's a surprisingly difficult skill. It's often harder to break up with someone than deal with being let go yourself. In the latter case, unless you're an egomaniacal crazy person, you move on. It's over, and you know that trying to force a relationship down a one-way street is an exercise in frustration for both parties.

Plus, if you keep trying, you're showing no respect for your intended, and no respect for yourself.

On the other side of the coin, it's hard to cause someone pain by having "the talk." I had to do it a few times. While these weren't great experiences, it was far better than continuing with something that wasn't working. Being alone is preferable to a difficult situation that won't improve.

While it sucks to be let go, the pain is brief. One piece of advice I have for those who are let go is to simply accept the decision. Don't try to argue your way out of it. Don't try to "fight" for something that doesn't really exist. Don't try to project your feelings of nostalgia and fondness onto your former partner. Your perception of the relationship is obviously different from his or her perception. Respect the breakup.

Above all, don't look for closure. You won't find it. I rarely gave a woman an honest answer in my reasoning behind the breakup. Why add to the hurt? I always turned it around on me. I'm sure the more intelligent of my former partners didn't buy it for a second, but most of the time when infidelity isn't involved, a breakup is over something that really isn't someone else's fault. It's just a realization that something isn't working.

When you have the skill and the confidence to let go when things aren't working, you will experience much more success in dating and you'll be far less afraid to let go of your ego and give a relationship a real chance.

Section 23: Conclusion

Hopefully, I've provided a little insight into the dating process. This handbook isn't for everyone, nor does it contain any magic formulae for those who agree with this advice.

I've outlined an approach to dating that worked very well for me. That's not to say I followed my own guidelines perfectly every step of the way. There were times when I was distracted by recovery. There were times when I was distracted by others I had dated in the past. I tried my best to always act with integrity, and keep my focus on relationships that had potential for long-term success. To do that, I always tried to view the relationship from my partners' perspectives.

The end result worked. I can honestly look back at my relationship with my wife, all the way back to our first contact, and see that it was a natural discovery and dating process, and led to what we believe is a life-long connection.

I wish everyone out there success in reaching their relationship goals, and happiness in whatever path they choose in this journey.

This is so great. Thanks for taking time to put it all in writing for us.

I'm still not ready to date, but have recently started wondering how people go about it after being out of the game for so long. I've heard it's a very different world than it was 10 years ago when I met the ex.

I'm one of those people that likes to have an idea of guidelines/boundaries before going in to situations.

Your handbook has answered a lot of my questions and I'm sure I'll refer to it often once I'm ready to get back out there.

Hi Red Sox Nation; I remember your dating spreadsheets It makes sense that you would want to write a dating handbook.

I've never been one to follow the book, but I'm happy to see you back, hope you can help some of the new folks and am very happy that you've found someone to love. Welcome back

Love this! I haven't read it all, but every bit make sense for me. I too remember your spreadsheet, and if you weren't already in a relationship I'd introduce you to my coworker as she does too!!!

Hi RSN! nice to see your name. Great idea! I hope it helps people!

Hi RSN, I remember your dating spreadsheets too. I appreciate your entry as a "inside the mind of a guy" dating handbook. Like studying a foreign culture through a study of the dating ritual, it is useful to me! Thank you.

Glad you are happy!!

Hi RSN, I remember your dating spreadsheets too. I appreciate your entry as a "inside the mind of a guy" dating handbook. Like studying a foreign culture through a study of the dating ritual, it is useful to me! Thank you.

Glad you are happy!!

Thanks.

Although men and women usually play different roles in the dating game (initiator versus invitee, sex-crazed junkie versus gatekeeper), our goals and desires are often remarkably similar.

The great secret of dating is really just to have confidence in who you are and enough introspection to pursue the best possible partner.

Neither is easy, though. Far too many of us conflate confidence with ego.

Thanks for this handbook. It answered a lot of my questions and cleared up quite a bit of confusion for me. I think it should keep being bumped to the head of the forum. Maybe even a bit of a healing library type of post for newcomers in NB.

Thank you sir.

Good to see you around again RSN, and really happy for you and your wife. Congrats and best wishes!