Q & A "I'm Dating Other People..."

Q: Dear Pella,

Now I'm sort of dating these 2 I met at a party and one I met through a friend. That's a bit confusing, as I'm developing more feelings toward one of them, but I'm not sure yet if he is a realistic choice for me long term. I need to know more. The other one might be a much more realistic choice, but I'm not having the same kinds of feelings. I do think things could potentially develop, but again, I need to know more...

In order to honor my process, I'm in this unfamiliar territory of dating both of them, without either of them knowing about the other. I am a highly honest person, so this feels somewhat dishonest or deceptive. Especially because I've gotten much more physically involved with one than the other (although I haven't had sex with him yet.) Hope that's not TMI.

So my question is: is it okay to date more than one person at a time, and if so should you tell them you are doing that? It feels somewhat deceptive not to, yet it seems awkward to tell them too...



A: Dear Sophia,

In the modern dating world it is assumed that everyone is free to date other people (and probably are) unless/until stated explicitly otherwise. That said, there are certain behaviors that can lead people to assume/expect/hope that things are exclusive. Once you get into this territory, I think that to be in your full integrity it's important to dispel any false expectations and be clear that you are dating other people.

When might someone assume you are dating exclusively? When at least one of the following is happening:

* You are in contact every day or almost every day.

* You see them in person several times a week.

* You are getting physically intimate (this line is different for everyone, but certainly before you have sex or exchange bodily fluids aside from saliva).

* You meet their friends or family or they meet yours.

* Someone says "I love you".

* You are making plans far in advance (upcoming vacations, etc.)

* Someone gets a key to someone's place.

If you're in this territory, or beyond, and you're dating other people, then I think it's important to let the other person know. If you've only been on a couple dates and haven't taken off your clothes yet, I think it's OK to keep it to yourself for now.

Of course, why you're dating other people when things are getting more serious with someone is another question. But we'll leave that exploration for a future blog post. Let's assume for now that you've thought it through and it makes good sense for you and your life goals right now. (Of course, this is all predicated on the idea that you're eventually shooting for monogamy. If you're not, then I think it's important to be up front about being polyamorous (or however you define yourself) right from the start, like date #1).

You mention that it seems awkward to tell them. Yes, it might be. That's OK. You can handle it. And you'll feel much better once you do.

Do be prepared for hurt feelings or push back. Be clear about whether this is something that is likely to change soon or not. If you don't see a future with this person, and they start asking about that, be honest. You will save them a lot of heartbreak and you can both move on to a relationship that's a better match for you.

Here are some sample phrases to get you started. Use your own words, and make sure that you're not implying something (e.g. exclusivity in the future) unless you feel that it's a real possibility.

* Since we've been seeing each other so frequently lately I wanted to let you know that I'm not ready to be exclusive.

* I just wanted to make sure you know that I'm dating other people to avoid any misunderstandings.

* I'm usually monogamously oriented, but I thought you should know that right now I'm currently dating someone else as well as you.

* Since things are kind of heating up between us (or 'we're starting to get more serious'), I want to let you know I'm involved with other people, too.

* Before we have sex, I thought you should know that I'm sleeping with other people. Are you OK with that? (Only ask if you're ready to hear the answer!)

* Thanks for the offer of the key to your place. I wouldn't feel comfortable taking it without letting you know that I'm actively dating another person. If you're okay with that, I'd be honored to take your key.

Yes, it's that simple. Scary? Perhaps. Awkward? Possibly.

You got this.

Best of Luck,


PS - TMI? No such thing! I'm all about relevant details, especially when we're talking about sex. You can't scare me off, trust me. And if you can't talk to your Dating Coach about your sex life, how are you going to get good feedback?

inspiration & insight?

Looking for more clarity, confidence & connection?

Sign up here for free dating inspiration and tips delivered straight to your inbox.

Plus, get my Top Ten Ways to Find Lasting Love.

Q & A:“Is the advice to let the guy lead still good advice?”

Q: Hey Pella, I've had 4 dates with a guy named Matthew whom I met at a party...

read more »

Q & A "I'm Dating Other People..."

Q: Dear Pella, Now I'm sort of dating these 2 guys...

read more »

Why Lovers are Like Food...

Imagine you are really hungry. You skipped breakfast and lunch. It’s 3 PM and your stomach is screaming “Feed me, feed me!”

read more »

Q & A: "So, um, are you looking to settle down?"

Q: Dear Pella, When is it okay to start asking questions about your date's hopes and plans for the future?

read more »

Q & A: What do I do while I wait? Should I settle?

Q: Dear Pella, What do I do in this time leading up to finding a partner and starting a family?

read more »

Q & A: When do we move from online messaging to an actual date?

Q: Dear Pella, A J-Dater has corresponded via J-Date email back and forth five times...

read more »

Are you ready to take the plunge?

Questions to ask yourself before committing for the long haul.

read more »

Do You Know Your Attachment Style?

When I work with a new client, one of the first things I help them determine is their attachment style. read more »

Top 18 Reasons to Run the Other Way

The heartache - or the relief - at the end of a relationship.

read more »

Do you suffer from Dating Fatigue Syndrome?

There’s a syndrome going around among many of my clients that is as normal as the common cold. I’ve dubbed it Dating Fatigue Syndrome.

read more »

Jennifer’s Letter to the World

Written by my client Jennifer, used with written permission.

read more »

How to Love Your Inner Ugly Duckling

My client Isabelle* is a beautiful 45 year old woman.

read more »


I’m sharing about my personal story today. It’s vulnerable to write about it, but I think it’s really important for you to know, so I’m going for it even though it's a little scary. Thanks for reading with an open heart.

read more »


The holidays can be a really lonely time when you’re single.

read more »

Breaking Up is Hard To Do

We've all been there.

That awkward dinner, painful phone call, or even the surprising email (true story).

read more »

4 Principles of Empowered Dating:

1. There is nothing wrong with being single.

It is possible to have a full life while single and that is a legitimate choice. Some people choose this for certain periods of time, some for the long term.

read more »

How Do You Stay Inspired to Keep Dating?

It's hard to stay inspired to keep dating if you are in a place of hopelessness or fear. If you're sure you're not going to get what you want, why bother?

read more »

Why Self-Care is a Radical Act (and Why "Selfish" is a Good Thing)

First of all, let's define what we're talking about. What do I mean when I say "self-care?"

read more »

Like this article? Sign up for's FREE!