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A number of articles recently have addressed the subject of dating when over 40. They all say it’s different than dating in your 20s and 30s.

You’ve finally met the perfect guy. Too bad he’s already dated your friend! So is he totally off limits? Or is there a way to turn “sloppy seconds” into a real relationship that even your friend can support?

Jennifer Oikle, Ph.D., relationship psychologist, dating coach, and founder of MySoulmateSolution.com explained what you need to consider before dating a friend’s ex. The number one rule, she says, is respect.

“Men may come and go, but friendships are rooted in trust. So whether or not it’s cool to date your friend’s ex is entirely dependent on your relationship with her and how she feels about it.”

First, she suggests, ask yourself what kind of relationship this guy had with your friend. Was it just a quick fling or were they planning to walk down the aisle? Also, what’s your personal interest level going in? Do you think he could be “the one” or are you just looking to have some fun?

Next, have a conversation with your friend–and let her know your intentions. Dr. Oikle says if it’s just a casual friend, you might simply inform her you plan to date her ex. But a close friend requires a little more. “I feel like if you are good friends, then permission should be obtained because you already have a real relationship with her–you just hope for a relationship with the guy. So, the first relationship should take precedence–getting the respect it deserves.”

Of course, don’t be surprised if she doesn’t approve. “Some people think it’s never OK for a friend to date their ex, others think it’s fine, others think it depends,” says Dr. Oikle.

In any case, avoid the temptation to sneak around behind her back. “Because she is always going to find out–and the feelings of being betrayed are always worse and more difficult to forgive and get over than whatever the behavior was to begin with,” she insists. “They might have been OK with you dating him, but can’t forgive your dishonesty–because that changes the whole level of trust and respect in the relationship.”

It may just be a matter of time–waiting until your friend feels “over” her ex, “when they can think and talk about him without triggering a reactive emotional response.” If not, and she still has feelings, “it may be just way too painful to continue the friendship, even if she agrees for you to go ahead from her logical side.”

One thing to keep in mind–breakups have ups and downs–which means she could feel “over him” one day and not the next.

“The most important thing is to stay sensitive to your friend and stay empathic to her feelings. What you did may not be wrong, but you can still be a shoulder to lean on and offer your support,” she says. “You can ask what she needs to feel better, and then see what you need to feel good within yourself, and then find the boundary that will work for you both.”

And what if it comes down to an ultimatum? Her or the ex?

“You can let her know that you really don’t want to have to choose, that you don’t think that’s the best outcome. But ultimately you might have to–and your heart and gut will tell you what is right, depending on the level of your friendship and the potential of the relationship,” says Dr. Oikle. “Is it okay to lose a best friend if you gain your husband? Maybe so. Is it okay to lose a good friend for 6 months of an up and down sexual relationship? Maybe not.”

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