Not much is happening in my dating life so it’s a good distraction when a friend reaches out for dating advice.

My friend Lauren’s dilemma: She’s enjoying conversation and flirting with a friend/colleague who wants to move the relationship to the next level. She knows a relationship with this person would not work and that a fling is also problematic. The situation is complicated in several ways.

Lauren, who is separated and actively planning her divorce, called to discuss the situation and bounce around some possible scenarios. Names and identifying details have been changed.

Have some fast and crunchy baked cod while I share my friend’s situation.

Lauren’s story reminds me of times when I have encountered decision points in my dating life. I knew what to do about a certain guy but I was tempted to go in the wrong direction. I needed a friend to reinforce my better instincts.

A couple of years ago, Lauren hired Joe, a landscape contractor at the hotel she manages. What started as a collegial work relationship has advanced into a friendship. Recently there has been a lot of banter and flirting and Joe frequently suggests that the two should talk over a particular problem at dinner or happy hour sometime.

Joe, who also does landscape work for Lauren’s soon to be ex-husband, knows about the couple’s marital situation. In fact he offered to be a witness in their upcoming divorce hearing.

Joe is 11 years younger than Lauren, less educated than she is, and is a hard drinker with a bad boy past. “He’s not relationship material,” she says. “The problem is that he’s attractive, has a great six-pack — despite too many six packs–, and is a really nice guy.” A few days ago, Joe texted her and invited her to a happy hour.

This was a clear invitation – not like previous ones that were more indefinite. Lauren is tempted by the possibility of a romantic fling but knows she should say no. She’s wondering how to decline his invitation without losing the friendship or offending him in any way. And she’s sad that if she turns down the happy hour, the flirting that she’s enjoying so much will likely disappear.

“How about if I just tell him I’m too busy right now getting ready for a holiday visit from my relatives and that getting together in the new year is more feasible?” Lauren asks.

“This leaves open the possibility that you’ll go out with him,” I suggest. “You’ll have to clarify your intention at some point – either now or the next time he asks you out.”

Lauren sighs. “He’s too young for me – even for something short term.”

“If he was fling material, his age wouldn’t be an issue- and might be an asset,” I say, “but he’s not good fling material. You’ve got a work relationship you don’t want to mess up and you’re counting on him as a witness in divorce court. You need a less complicated scenario for an ideal fling.”

I suggest she respond to Joe’s invitation in a way that acknowledges their friendship but removes the possibility of dating.

I propose a potential response: Sounds like fun but I’m super crazed right now getting ready for my visiting relatives. Happy to get together as friends in the new year. I like to be clear and want you to know that I’m not ready to date. Plus I value our friendship and I would not jeopardize it.

I don’t know what Lauren wrote to Joe but she reported that she successfully turned down the invite and was able to maintain collegiality and friendship.

Have you navigated a challenging dating scenario? How did it go? Let me know!

Until next week, happy dating or not dating.

XXXOOO

Nadia