Dear Rocky Love: 5.7.14

By on May 6, 2014
Rocky Love
Rocky Love

Rocky Love


Dear Rocky Love,
I have newly developed romantic feelings for a friend of eight years. We have always been flirty but gone our separate ways in love. He lives outside of Jackson and every time we meet up it’s a blast and a little ambiguous if we are on a date or not. Then we stay in touch, swapping pop culture tidbits and chatting but it eventually peters out. I don’t want to make our friendship awkward, but I would like him to start seeing me as a potential mate with sexy prowess! What can I do to empower my situation … considering he may not feel the same?
– Signed, Stuck in the friend zone

Dear Stuck,
It depends how serious you are in your quest for a mate. If it’s a top-of-the-list priority and this guy has good potential, then I think you should see if the relationship would develop. Jackson has such a limited dating pool, and you wouldn’t be the first person to search outside the Hole for a soul(mate).

The limits of local dating could also be a reason to do nothing and keep this handy flirtation in your back pocket for times when things aren’t working here. Then you’ll always have your out of town guy to call or text for a little no-strings romantic energy.

If you are seriously looking for a partner, here’s how to do it without risking the friendship: Think of the potential romance as a ping-pong game. Next time you “ping” make it a little bit more flirty or direct, but not too much. Maybe a, “Hey, that was so fun the other week when we saw each other, I almost kissed you good night!” Okay, maybe that’s too blunt. You could try asking some innocent questions about his romantic life. Find out if he’s dating anyone. Find out what he’s looking for. If you ask these questions in the context of friendship, then you don’t have to put yourself out there too much if you aren’t getting responses that open the door further. His “pongs” should mirror or slightly increase the romantic-ness. Then you safely deepen the connection together.

Now that’s my sensible advice. Rocky Love herself is classifiably impetuous and overly curious. For the sake of fun, I can tell you what Rocky would do: Rocky would announce something like, “Wow, I have a big crush on you!” The logic being, what have you really got to lose? If your dude is really into you too, you’re not going to muck things up by letting him know you want to get closer. You’ll be doing you both a favor. And if he’s not into it, then you find out sooner without getting yourself all strung out.

I can attest that Rocky Love’s style has worked for her more than it’s hurt her. I’m a proponent of the theory that with every relationship we learn about ourselves. Also, I think hearts grow stronger, not weaker, by enduring some bruises.
So, it really is up to you how you want to play it. Are you feeling self-protective? Then go for the sensible advice. Are you feeling adventurous? Then go forth and let him know you want to jump his bones.

– XO, Rocky Love

Dear Rocky Love is an advice column on dating, sex and relationships in the Tetons. Send your letters c/o JH Weekly, PO Box 3249, Jackson, WY 83001 or email:

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