Photo Credit: Jewish Press

Dear Dating Coach,

A great guy was just suggested to me and he sounds amazing. We have reached out to his references and others who know him and everyone says that he is outgoing, hardworking, and fun-loving; all qualities that really appeal to me. But when I told a good friend of mine that I would be going out with someone new, she told me she had dated him. She said they went out a bunch of times but both decided they were not interested in moving forward. Now I feel awkward. We are really close. What if I marry this guy? Wouldn’t that be strange? Ugh. Should I just say no?

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Dating Around

 

Dear Around,

It’s a Tuesday afternoon and dinner is simmering on the stove. The house is peaceful and calm. The children are playing angelically together, the house is spotless, and the mother is humming a pleasant tune at the stove. (Ok, maybe someone is throwing the ‘mancala’ pieces across the room because ‘he cheated,’ and maybe someone just dumped an entire box of matchbox cars on the floor, and maybe the mother is actually ‘deep breathing.’ Whatever. Go back to my beautiful scene please.) The incredible aroma wafts through the house beckoning the family to the table. The clean and polite children sit pleasantly at the table happy to eat what they are served. (Ok, yes, that is a weird stain on her uniform shirt, forks are not supposed to be optional, and maybe someone already spilled their drink. Semantics! Go back to my scene.) The children take a bite of dinner and violently recoil in distaste. “I will not eat this. This home-cooked, nutritious, and beautiful dinner is a disgrace to dinners everywhere.” They race to prepare a dinner more in keeping with their high standards (bagels and cream cheese, cereal and milk, or pasta with cheese, but not that cheese.) The parents calmly (poetic license) take their places at the abandoned dinner table and eat everything with glee. A quiet dinner? Just the two of us? Date night!

 

It’s Ok If You…

Thank you for your letter. This feels like a complicated position to be in and you are not sure what to do. You are certainly excited about this prospect, but worry that you will be uncomfortable in your close friendship if this works out. You can already picture the future “awkwardness” in their interactions should this go in a positive direction. Is it strange you wonder, to date a guy that someone you care about deeply has already dated? Perhaps it is safer to simply walk away.

 

Don’t Like Me…

I get it. No one likes to feel uncomfortable. You understand that your friend did not continue to date this guy because they both mutually agreed it was not the right fit. She did not have anything negative or worrying to share about him. Yet, you are still thinking about walking away from a guy that sounds like he might be the right fit for you.

 

Not Everyone Has Good Taste.

There are really two parts to this. First, if you are so blessed as to marry this guy, you will likely get past any hint of awkwardness with your friend fairly quickly. She only dated him. They moved on and so will any hint of discomfort. Second, even if it continues to feel strange when she is around, it does not warrant not dating someone who might be your zivug. A marriage to the right person will definitely trump the “chance” that you might feel “weird” around your friend. (Additionally, may I suggest a more discreet approach to dating in general, where it is unnecessary to share “names” with your friends before you even connect with someone.) Finally, grab this opportunity with positivity and enthusiasm as a FIRST chance for you to meet the right person regardless of anyone else’s taste and experience. This is a moment you don’t want to pass up. So, sit down and enjoy the date night.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at [email protected] to schedule a phone session.