It’s Never Too Late for Authenticity
Dear Jordan,
I had a huge crush on my co-worker but I never made a move because she was in a committed relationship. They split up, we went out for a few drinks, and seemingly against all odds, we had a one night stand. That was 7 months ago and we didn’t really discuss it afterwards. She is no longer a co-worker but I still have these feelings for her. Is there a ‘right’ way to bring this subject up?
– Smitten from a One Night Stand
Dear Smitten from a One Night Stand,
I do not think there is a “right” way, but some ways are better than others. In general your best bet is to be as specific and honest as possible about what happened and how you feel. This will serve your own awakening while opening the door to intimacy and trust.
So, the first step is to get clear about how you feel.
What Happened?
Some strong force has kept you interested for seven months, yet an equally strong force has kept you shy. What holds you back from reaching out to her? What are you hopeful for and what are you afraid of?
The very things that have kept you blocked can be the keys to getting what you want. By becoming more clear about the forces at work in your psyche, you can more clearly communicate with excitement instead of remorse or blame.
Discover What You Care About
For example, let us pretend that you did not follow up because you were afraid of rejection. Whatever the reason for the fear (you were co-workers, you were rejected in your past), there is a deeper underlying truth: You really like her. If you didn’t care about her, you wouldn’t care about rejection.
Max Attractiveness = Strength + Vulnerability
If you can can clearly communicate how you feel about her and what happened to block you from expressing that care, you will demonstrate the rare ability to be both a strong and vulnerable man.*
You will show that you are secure even in your insecurity, which most people find deeply attractive.
And you will invite the vulnerable truth from her, so if she does reject you, you are more likely to hear the real reason why, allowing you to improve instead of having to always second guess yourself.
What To Do: A Sample Conversation
If you do not have a chance to see her in person, I recommend a phone call because it is a better medium for expression emotions than email or text. The following text will give you an idea of how I might act in a similar situation, but it has been approved by two female editors.
Jordan: Sally, hi! Um, it is Jordan, you know, from work. (ideally less “ums,” but realistically a little uncertainty is not a problem)
Sally: Oh yeah, hi Jordan. It’s been a while.
J: Yeah, it has. I’m a bit nervous because I know this is a little out of the blue, (acknowledging the circumstance and how you feel is likely to put her at ease) but I was just thinking about how much fun I had that night at the [insert bar name]. I still can’t stop laughing about that goat story. (Some specific action and the specific way you feel about it. Depending on how racy you want to go and how comfortable she is with sex, you might even refer to the one night stand—with bigger risk often comes bigger reward)
S: Oh, really?
J: Yeah, in fact it was precisely because I had such a good time that I never called you. I’m sorry, I was afraid of rejection. It’s much more important to me now to see what might develop between us because I still really like you—are you available Saturday for lunch at the [insert nice place that isn’t too expensive]? (Use the words that feel good to you, fess up to what happened, throw in a compliment if it is honest and you are really feeling it in the moment, and then offer her a specific time and place to meet up that is low pressure but still classy)
S: I’m not available Saturday.
J: What about a coffee Friday afternoon at [insert coffee shop name]? (Might be a good idea to have an even lower pressure back up plan)
S: Sure.
J: Great, see you then!
From there, I recommend trying to maintain your honesty, specificity, and staying connected to the care you feel. But most important of all, be yourself—if she does not like the real you, you probably will not be a good match.
Good luck!
*This strength and vulnerability is prized in a woman too, and I believe this advice would apply to same sex/transgender relationships just as well.