Wendy,

I’m a 48 year old divorced man juggling three women. I like all of them for different reasons.

The first is semi-attractive but she makes me laugh nonstop and we have the most amazing time together, the second is drop dead gorgeous and whenever I go out with her all eyes are on her and I feel like I am on top of the world, the third one is what I call the underdog but she is the greatest sex I have ever had in my entire life. I am ready to settle down. What do I do? Whom do I choose?

– AT A LOSS

Dear At A Loss,

Well,  I have thought a lot about how to respond to your question. I’m sure you know in your head the logical answer, along with anyone else reading this. But, it’s not that simple.  You have to decide what is the most important thing in a relationship to YOU.

When you mentioned each girl, you mentioned the attributes that you liked:

One girl is drop dead gorgeous. You like the way you feel when you are out in public and people see you together. But how do you feel when you are alone with her? You will spend more time alone with a partner than out in public for everyone to see. Does she make you smile? Is there passion between you? Is she beautiful on the inside too?  Will she be there for you when you need her? If she lost her beauty tomorrow could you still love her and be with her?

One girl was the greatest sex you ever had, but what about when you are not having sex?  Can you talk about things with her?  Do you have fun (without the sex)?  You will be spending more time out of bed with a partner than in bed (I assume – if not, that is a whole other issue). Can you see yourself growing old with her?  Great sex is great, but is that enough to sustain a long term relationship?

The third girl you shared the most attributes that you liked about her. You are attracted to her, she makes you laugh and you have a great time with her. Is there passion with this girl? Can you build a life with her?   She sounds like the whole package.

You have to decide which girl you can see yourself with in 10 years.  Who will be there for you? Who you are most compatible with in ALL aspects of your life? If sex is the most important thing in a relationship to you, then pick the one that is the best sex that you have ever had. If being seen with the hottest girl around is most important, then pick her. I cannot tell you which girl will make you the happiest. You have to decide that.  If you are truly looking for a long term relationship then think about who you are most compatible with to get through the hard times together.

I can’t tell you who to choose, but just so you know…I am rooting for the girl that makes you laugh and that you have the best time with.   😉

Wendy Wiener

Wendy works as a marketing analyst for a commercial real estate firm. She is a divorced mom of two teenage daughters, who is soon to be an empty nester as her younger daughter goes off to college. After sharing all of her crazy dating experiences with her friends over the years, they have finally convinced her to write them down and share them with the world. Wendy believes one day she will find her perfect match and is enjoying the crazy ride until then.