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Dating in NYC: Top 10 Tips for Dating Multiple People

Date: January 9, 2014
Author: julietjeske
Categories: Dating, Dating - NYC, Dating After 35, Dating Online, New York City, Relationships, Social Media, Uncategorized
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Before I even tackle this subject I will openly admit I’m a solidly monogamous person.  As I’ve written before the whole idea of multiple lovers, hookups and sexual relationships with near strangers baffles me.  I can’t keep several plates spinning while I’m trying to write this blog, work on my memoir, get stage time in New York City and pay my rent.   I’m writing this though because this issue comes up all the time, and I’m annoyed that most of the articles I’ve found about this topic are written only for men.  I’ve based these tips on experiences I’ve had and what a lot of my friends have gone through.  I not advocating for any style of dating, nor would I say this would work for every person.

There are many variations on dating multiple people, too many to list here really.  The key to having multiple partners should NOT be about lying, sneaking around and deception.  Lies are evil.  As I have said before:

I would rather have an honest sinner than a phony saint.

The following are just guidelines.  It’s really about what any two people are comfortable with in any partnership.  If you only have sex with a person once, they really don’t need to know much.  But if you are seeing more than one person on a regular basis, communication is key to keeping everyone happy.

1. Let a new partner know early on that you are not looking for a sexually exclusive relationship: Of course this can change as the relationship develops.  Neither partner should assume though that a casual open relationship will turn into a committed monogamous one. When in doubt – communicate.

2. Avoid getting involved with people who aren’t also honest with their primary partners – A friend who has been polyamorous for years put it to me this way.  “I avoid being the ‘other’ woman.  If a man tells me he is in an open marriage, I tell him I will have to speak to your wife about this, just to make sure”  It might sound crazy, but if the couple is in an open marriage, this sort of request probably happens to them all the time.  It’s better to make sure everything is above-board, before you find some woman calling you a home-wrecker or threatening to kill you for sleeping with her husband.

3. Don’t assume one lover wants to hear details about any others – Some partners honestly may not mind this, but not everyone is different.  One woman might not want to know that another regular partner is younger, thinner, lives closer to you or has a cat.  If these relationships truly are separate, then there is no reason to share this sort of information.  Simply establishing that you are not exclusive is usually enough.  If you want a change in your relationship, then let your partner know.  NEVER ASSUME ANYTHING! 

4. Always use protection – If you are having sex with multiple people – DON’T BE AN IDIOT.  Use condoms and practice safe sex.  Other than the usual STDs we all fear, there is a strain of antibiotic resistant Gonorrhea going around New York City that is all sorts of awful. Spreading STD’s is irresponsible and reckless.  If you want to have condom free sex, then maybe you might want to find one primary partner and at least use condoms outside of the main relationship.

5. Beware of Social Media – If you tweet naughty messages to one woman know that anyone can see it. You don’t know who knows each other or which partner might be a regular cyber sleuth.  Facebook profiles are even more transparent – comments, likes, even old conversations with partners are there for life unless you remove them.  A simple comment like, “You are so beautiful” could get you in trouble if you post it where another, more neglected lover, could see it. Basically you have to treat all comments on social media as if you are standing on top of a mountain declaring them for the universe.  The internet holds no secrets.

6. Don’t treat you casual lovers like girlfriends/boyfriends – Again there are no hard rules to this, as some polyamorous relationships are anything but casual.   This is the number one complaint I get from both men and women about casual relationships.  You can’t expect someone who you see only for sex on occasion to get that emotionally invested in you.  They aren’t going to necessarily want to meet your friends, go to social functions with you, listen to your neurotic ramblings or bring you chicken soup when you get a nasty cold.  When these lines get blurred, people are more likely to get their feelings hurt.  Anyone can have a primary relationship and still have multiple lovers on the side, but not without some boundaries first.  You should never assume a regular hook-up is a girlfriend, or even wants that role.

7. Treat everyone with respect – This should go without saying in every dating situation.  I’ve seen a lot of alarming language on dating sites, where a man or woman will go on and on about their primary partner and then send an email that is just rude and inappropriate to a total stranger.

8. Don’t make anyone feel like they are last on your list – This might be OK with some partners, but overall you don’t want to make a person feel like you literally called up three or four people before you decided to settle on them.

9. Don’t complain about other lovers – This is just rude behavior.  If a woman complains to a partner about another man she is seeing, he is likely to assume she will turn around and do the same thing to him.

10. When in doubt communicate – Of course you can lie and sneak around, but there is a good likelihood that you’ll get caught.  When you get caught a betrayed lover might slash your tires, show up at your workplace and scream “Whore” as you walk down the street, stalk you or one of your other partners, text you incessantly for hours, post naked photos of you online, write Facebook statuses trashing your name, or even threaten you with physical violence.  Deception brings out the worst in people.  Some people are emotionally unstable, mentally ill, cruel, narcissistic or have deeply entrenched personality disorders.  No amount of open communication can prevent a person from reacting in a completely irrational or psychotic way.  However a string of lies is more likely to make a perfectly well-adjusted human being buy a ticket to a place called crazytown.

It’s really up to you and your partners – Other than practicing safe-sex and respect, it’s really up to each person.  When in doubt be open and COMMUNICATE. Some of the biggest problems in any relationship come from not understanding what both partners want.

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Dating Online – Mr. Let’s Keep it Casual

Date: February 5, 2011
Author: julietjeske
Categories: Dating, Dating - NYC, Dating After 35, Dating After Divorce, Dating Online, New York City
Comments: 4 Replies

My article about men that I have dubbed the “Wife Shoppers” was so popular, I thought I would keep it going with their counterpart….Mr. Let’s Keep it Casual. I have also called them “Player Light”

  • Age – Any age, but then tend to be younger…under 35
  • Marital Status – Most have never been married
  • Most have no children – although they come in all types
  • Usually attractive and in shape, but not always
  • Not liberal with compliments towards you in any way – This would give you too much power in their minds, so don’t expect a lot of praise or adoration
  • Emotionally distant

The Introduction – Early into the correspondence, or into the first meeting of “Let’s Keep it Casual” the man will lay his cards out on the table.  A technique that some of my male psychology books call….announcing the exit strategy.  The give you the endgame before the game has even started lines like

  • “I don’t get emotionally involved”
  • “I like to keep things casual”
  • “I am not looking for anything serious”
  • “I am really busy and I don’t have time to commit to one person”
  • “I like to date multiple women at the same time” – At least he is being honest, so if you are OK with that then go for it, just don’t expect it to change.
  • “My ex really messed me up, so I can’t bond with anyone on a deep level right now” – Sadly I’ve encounted a few men who just use this as a line.  Take this one with a grain of salt.

They are all basically saying the same thing.  Look, don’t even think about considering me boyfriend material.  I respect the bluntness and honesty, and they are laying the groundwork for when a woman might push for something more they will say, and mean it.

  • “Look, I told you where I stood before we even got together”

The Plan of Action – They might send a friendly text, always when they are already out, or available, usually in the evening or weekends asking What is up? They don’t ask personal questions, they don’t send personal emails of any length or importance.  Generally they don’t use the phone for anything other than text messages.  Most correspondence is just about getting sex when they want it, and on their terms. They are hoping that you will drop whatever you are doing, meet up with them.  They don’t have to take you out to dinner, or a movie, they don’t have to spend any real time getting to know you, they don’t have to spend any money on you except maybe a few drinks and they get sex when it is convenient for them.  I call them “Player Light” because unlike a player, at least they are fairly upfront an honest about their intentions.   So if you are open to a sexually based relationship with little else….these boys might be for you.

The reality though, is that these relationships rarely work out according to plan.  Now I have plenty of friends that openly live a polyamorous lifestyle of having several lovers scattered all over the city and they are perfectly happy with that situation.  Not everyone is happy in a traditional monogamous relationship, and they aren’t meant to live within the constrains of one.

What tends to happen, is that Mr. Let’s Keep it Casual might end up treating you like a low grade girlfriend.   If a situation like this goes on long enough, the man will ultimately start dumping his emotional baggage either before or after sex.  But he set up such rigid standards on the relationship, don’t expect that he’ll be as open to you doing the same.  Most women engage in soul purging all day long with their female friends so it isn’t exactly unheard of for a woman to treat a man, especially one they are having sex with, in the same way.  Human beings aren’t robots, and our brain chemistry alone goes a bit berserk after an orgasm, so it is natural to bond on a deeper level with a sexual partner, especially after a period of time.   So good luck on keeping things completely unemotional with Mr. Let’s Keep it Casual, unless of course you simply “tap it” a few times and then never again.

If the woman takes the initiative and actually dictates when they “hang out” then Mr. Let’s Keep it Casual might protest that they are being needy.   Because so many times, Mr. Let’s Keep it Casual is really just saying I want what I want, when I want it, and if you aren’t cool with that, then forget it.  It is a selfish and immature way of dealing with a partner of any kind.

The biggest trap when dealing with a man like this is the concept of the magical power of the vagina.  Many think their winning personality and great sex will somehow win a guy over and CHANGE HIM!  Sure this could happen, but it probably won’t.  If a man tells you right off the bat that they aren’t looking for anything beyond a sexual relationship, they probably mean it. He probably will never see you in a different light because you entered the situation with the cards stacked against you.    And just because he starts to bitch about his problems at work or how his ex-girlfriend never understood him, doesn’t mean you have won him over.   If you want a no strings attached sexual partner, these guys might be perfect for you.  But if you want something more….keep looking.

One of the main things that attracts me to a man is his intellect and point of view, so a Mr. Let’s Keep it Casual, really bores me.  They won’t allow me to get to know them on anything but a base carnal level.  So at least for a girl like myself, they don’t really stimulate me all that much.  I like to be intrigued by a man, on a deeper level than simply wondering when the next text message of “What’s Up?“ is going to arrive.  When they use text speck such as “Hey grl what U doing?  R U kk?”  It’s like a million cold showers all at once.  If you are going to try to hook up with me, at least write in full sentences and use proper English.

The other trap is that a man who is in serious relationship or married might seek a casual relationship in order to cheat.  They won’t want to bond with you, because they are just using you for sex.  This has nearly happened to me a few times, luckily I’ve always discovered the truth before I fell for it.

When I’ve found myself on dates with guys like this, I just think of my own exit strategies.  I might make them think they have a shot with me, as it just makes the date much more pleasant.   They don’t know the minute I hear a line like “I don’t get emotionally attached” I have already given up.  The only people I can think of that really don’t get emotionally attached are sociopaths…..and do I really want to date one of those?

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