Dear Samara,

Is it possible to be in love with two guys at the same time? I am 26 and have been dating this terrific pro tennis player who I adore for about 9 months – he’s fun, exciting and we get along super well. Then about 8 months ago, I started seeing this guy that I work with every day. We click on all levels and in so many ways he is my soulmate. And yes, I am doing the wrong thing – I am sleeping with both of them and they are both incredible in bed. Since my tennis player travels a lot, I seem to balance out the time I can spend with each so the other doesn’t suspect anything. What the heck do I do?

Mariah in Love


My Dear Mariah,

It is possible to be infatuated with more than one person at a time. You can adore them both and, as mentioned, have a great sex with each. What you can’t do is establish a deep level of love and intimacy with a person unless you are being completely honest. Right now you’re digging two shallow holes instead of one deep one, which is fine if that’s what you want.

You’re young and it seems like you’re having fun, so one option is to keep doing what you’re doing—provided you’re upfront. Without going into great detail, let them both know that you are seeing other people and find out if they are seeing other people. I suspect that the tennis pro’s travel schedule might work for him the same way it works for you—making it easy to hide romantic rendezvous. You say that you’re doing the wrong thing by sleeping with them both. I only think that’s wrong if they are both under the impression that you’re exclusive. If it’s never been brought up, you can plead ignorance.

If you feel that it’s time to make a decision between the two for your own sake or one of the guys is asking you for commitment, then step back and imagine your life with only your coworker. Take your time. Try to think beyond the rush of fun dates and great sex (it’s difficult, I know). Now do the same with the tennis pro. Questions you can ask yourself: What do I hope to get out of a committed relationship? Can he provide it? Am I my authentic self with him? Do his values align with mine? Make lists if you must. Be thoughtful in your decision making.

No matter who you choose, you will have moments of wondering what it would have been like if you’d chosen the other. It’s natural and it doesn’t mean you made the wrong decision. If the relationship you find yourself in deepens in affection and honesty, then you are where you belong.





Samara O’Shea is the author of Loves Me…Not: How to Survive (and Thrive!) in the Face of Unrequited Love. She has written for Marie Claire and The Huffington Post.Samara is currently pursuing a master’s degree in social work at Temple University with the end goal of becoming a licensed clinical social worker and having her own therapy practice. Stop by and say hi at SamaraOShea.com.

Find Samara on: Twitter: @SamaraOshea Facebook: Irish Samara




Dear Caroline,

I never went to college. I am a single mom to three kids who I have put through college, by myself. My oldest daughter is very smart and very successful, and is embarrassed that I am not as educated as she is. She doesn’t say so, but does not want to be seen with me when with her friends. This is really upsetting me. How do I handle it?

Not such a stupid Mother

Dear Not So Stupid,

I hear your insecurity and hurt. It’s clear that you’ve got what it takes to successfully raise three smart and educated children, but is that enough for you? Let’s start with why you doubt yourself. I love to remind people that we are constantly projecting. Really, it’s a wonder how we make relationships work when we are projecting our own assumptions and perceptions on to everyone we come in contact with.

I challenge you to take some time to look at the deeper perceptions you hold of yourself, and how many of them you chose to believe are coming from someone else, including your daughter. Have you met your own needs around your educational development? When in the midst of an emotional conflict, it is always best to begin with the self.

‘The Four Agreements’ teaches us another beautiful lesson: don’t make assumptions. We tend to do just this when we believe we have something to lose, when we feel shame- it’s that ego trying to keep itself safe. So, consider where your own shame about not being traditionally educated might be coloring your view of the relationship and just how easy it is to assume that it’s coming from a source outside of yourself, because maybe then you don’t have to wrestle with yourself. Right? Understandably, such an assumption can be difficult to broach with a loved one, but worth it. Ask your daughter how she really feels and thinks about you. Then take it a step further, show her some deep honesty and vulnerability, and tell her how you expect she thinks and feels about you. Those expectations are pesky and ever-present, but when you sleigh them with truth and humility, you then have the capacity to deepen the relationships you have with anyone, in this case, someone most worth humbling yourself for. In sharing your pain with your daughter, you teach great lessons in strength, self-care, and courageous vulnerability.

It is possible that your daughter does feel this way about you, Momma. But what if she actually feels something like this for herself and she is simply mirroring this back to you? Women tend to carry around each other’s shame. Maybe you owe it to her and to yourself to look your insecurities in the face and speak some truths to each other. And perhaps, if you are projecting something, you might find that there is something entirely different going on, something worth learning about your daughter, perhaps feelings she may have about the disconnect between her own life style and yours. Education is powerful, but keep in mind that there are many ways to become educated. Learning about how to constructively express and address our personal wounds and conflicts suggests a high level of intelligence. Once you’ve gained the courage to have a conversation with your smart, successful, and likely understanding and very human daughter (with all of the same very human insecurities), maybe it’s time to consider whether you want to delve into a new scholastic adventure. Are you happy with where you are or are you ready to take on something new that may produce some feelings of empowerment? What’s a realistic standard for what you want, and how might you meet that goal? If shame is something that’s coming up for you then this might be just what you need to cultivate some pride. We can all benefit from a shift in attitude that allows for a little self-love. Just imagine what this model could do for your relationships with your kids.If nothing else, our fears and conflicts are wonderful teachers and guides, providing great insight into the parts of ourselves we tend to quiet.




Caroline Wales is a Certified Holistic Life Coach and a PhD candidate in the field of Transpersonal Clinical Psychology. Her focus is in helping individuals learn to identify their strengths and to utilize tools and skills in coping with whatever life throws their way. Caroline’s philosophy is that with the practice of intention and the desire to go deeper, coaching can help provide insight into recognizing one’s own personal power, and to teach individuals how to tune into the body-mind, energy, and spirit, as a practice of loving and supporting oneself.

To contact Caroline: cawales28@gmail.com – Facebook: Caroline A Wales -Website: Caroline A Wales



You can ask Samara and Caroline questions for the Love & Life Column here at folks@thedailybasics.com.

* The ideas and advice presented here are not a substitute for professional advice. Talk to your psychologist, counselor, physician or health care professional for situations that warrant further analysis.