Sami Holden determines the best way to help two friends realize they are perfect for each other.
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Dear Sami,
I know two friends who would be perfect together, but there is a minor problem. The guy is interested in the girl, but they casually dated a few years ago. She decided he was selfish and he even admitted that he didn’t take their relationship seriously. Now he is wishing he had been kinder and hadn’t taken her for granted. She is fresh out of an eight-year long relationship that isn’t even completely cut off. What should my friend do to win back this amazing catch?
Also, this seems like a matter of figuring out good timing. How long should my friend wait before making a first move? She has already created a profile on Match.com. None of us know if she is serious about going on dates through the website or not, but it seems like she is making steps to find someone new.
Sincerely,
Looking Out for Friends
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Dear Looking Out for Friends,
Your question reminds me of a fruit roll-up…it’s going to need some unraveling. I haven’t been awarded a degree in solving dating problems, but I’m pretty sure it’s just because that master’s degree doesn’t yet exist. If that’s alright with you, let’s proceed in figuring this one out.
It sounds like a rom-com is playing out in front of your eyes. It’s great that you want both of your friends to be happy, but also keep in the back of your mind that it may not in fact make them happy to be together. What works in their favor is that you can gather information from both sides so neither one is having to fully put themselves out there. Also know this could maybe backfire for you, but it sounds like you’re invested. For the time being, I’ll buy into the fact that maybe they belong together. It’s been probably close to a decade since they casually dated. A lot has changed, and I definitely think that’s long enough to where they are most likely not the same people they once were. Things that were not meshing before might not be an issue now.
Let’s look at things from her perspective. Eight years is a long time to be in a relationship. That is the length of many a Hollywood marriage. What gives me pause is when you said “isn’t even completely cut off”. Don’t send your other friend into this! For any fresh chances to be had, she has to be done with the ex. Her being on Match.com means nothing. After being with one person for so long, it is likely she is seeing what is out there. Maybe she wants to feel the validation of being wanted by someone new without actually proceeding forward with a date. Attention can be intoxicating. Is she looking for someone new, or is she looking not to be alone? Those are not the same thing.
I had a friend recently ask me if two months was long enough after breaking off a couple-month relationship before dating again. I have notoriously been a bad person to ask about this. I was in a multi-month relationship a few years back and within a week after it ended was back out dating. Guys get a bad rap for promptly moving on, but it’s in no way a gender thing. I immediately fell for new guy because he was giving me the attention I never received from the ex. He wasn’t flaky. He told me I was pretty. Sadly, he also turned out to be the younger brother of my ex’s high school best friend. Oops! I had no clue. This quickly put an end to whatever had been building over those few weeks. The thing that was awful was I really liked him, but it was just too soon. This created a painful double break-up effect, and it’s probably the only dating experience I look back on with some sadness. He was great. It was not the right time.
Maybe your guy friend is the right option for the girl, but the time just doesn’t sound like it’s matching up. I don’t think there is a right time for him to make a move. Her being completely out of the relationship would be an important thing to consider. The guys on Match.com are irrelevant. If the guy friend really has something to offer her relationship-wise, other people frankly don’t matter. If she ends up with a Match.com guy, then it wasn’t going to happen for your guy friend.
However, your guy friend does have something to prove. It sounds like he might have been an asshat in his youth. It happens. He needs to show that he is a mensch (that’s basically a good dude for all you non-Yiddish speakers) now. Based on their history, she has no real reason to believe that he would be worth her time. You need to get them interacting. Get them both at social gatherings. Football party at your place? Just so happen to have two extra concert tickets available in the group that was going to hear a band play? Yes, it’s a little sneaky but it at least gives them a chance to get to know each other as grown-ups. Maybe your guy friend is still into the idea of your other friend from how he remembers her eight plus years ago. This gives them a chance to get to know the current versions of each other in a lower pressure situation. So I give you permission to meddle a little, but allow them to figure out how they feel about each other now. If there’s attraction between the two of them when they reconnect, it will unfold naturally as it should.
Here’s for better dating days ahead,
~Sami
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This post is republished on Medium.
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