Q & A Wednesdays: How/when do I have the relationship talk?

Posted by in love after 40, single women over 40 | 0 comments

Dear Sandy,

I am twenty-six years old, single and happy. I have had many relationships with men, but no one has been special enough for me to completely open up to. I don’t think I’ve ever really been in love. I have known Isaac for about five years.  We’ve been great friends and have an amazing connection, but we’ve never dated. Mostly, it’s because we’ve never lived in the same city for more than a week! Next weekend, he’s going to be my date at the destination wedding of a good friend. Now that I have a much more clear idea about what I’m looking for in a partner, I think Isaac and I might be a great match. I am wondering how to have a conversation with him about seeing if we should take our relationship to the next step and explore what’s there. What do you think? I am petrified to ask him if he sees us as a couple, but don’t want to miss out on knowing if I can have a relationship with such an amazing man. Help!


Dear Debra,

Taking a relationship from friend to lover can be challenging. Especially if you a) aren’t yet dating and b) live in different cities.

As archaic as it may seem, it is usually better for the man to be the one who lets you know he’s ready for a relationship. Trust me when I say that I am far from sexist. I believe strongly in women’s rights. But when it comes to relationships, we are usually still dealing with a caveman mentality; men hunt and women gather.

As a hunter, men need to feel ready to commit to one woman, and it is not always something they want right away. Monogamy is not hard-wired into a guy. I am speaking in general terms here, but women are much more relationship oriented. They want to connect. They want to see if he’s a guy they can have a long-term relationship with. Not just a fling.

Men are sexually oriented. Attraction comes first. Emotions follow.

Ultimately, a guy who is relationship oriented will want a woman like you, someone who is monogamous and wants to give of herself emotionally. If he feels great when he’s with you, he’s probably going to choose only you.

However, if the timing is not right, when you have the ‘talk’ with a man, you can scare him off.

My suggestion is that you see what happens at the destination wedding. If you want to see if he sees you ‘in that way’, be flirty. Touch him. Show him that you are interested in taking it to the next level.

If he makes his move, you can talk about how attracted you are.

Eventually, if you keep developing the relationship, you can talk about how frustrating it is to live in two different cities. Then, you can speak about how to deal with that challenge.

Don’t rush the conversation. Put your feelers out. Have fun. Flirt. And see what happens.

Best of luck to you. Let me know how it goes!





Leave a Comment

Your email address will not be published. Required fields are marked *

AlphaOmega Captcha Classica  –  Enter Security Code

This site uses Akismet to reduce spam. Learn how your comment data is processed.