DILEMMA: Being Chased by a Cougar, But Crushing on a Straight Woman #WhereTheyDoThat@?

The Cougar vs. The Straight Woman

I swear all of this just came out of nowhere! Like what the motherf*ck?!? Overnight something happened somewhere, somehow and I’m still in awe over it all. So I’ve been talking to The Cougar for a bit now – casual email, text banter back and forth several times a day, shameless flirting here and there – she’s hella sexy, in her mid-40’s, educated, sophisticated, accomplished, and for those of you who this matters for, she’s White. She was very forward during our first conversation, insisting that I take her number and “call or text me anytime, beautiful.” For those of you who don’t know, I LOVE COUGARS! There’s just something about a woman in that 35-45 age range that peaks my interest and drives me wild (in a VERY VERY VERY good way, check out my post entitled Ode to Cougars). When (if) I ever settle down, don’t be too surprised to hear that my Mrs. is somewhere within that age range.

Somewhere in the mix of my ever so willing chase with The Cougar, The Straight Woman (and let me clarify that I am not 100% sure she is Straight, she could be Bisexual or some other orientation) and I began to form a friendship. We share a common interest and it provides us ample opportunities to engage with one another. I honestly never looked at her the way I do now until we had a conversation over another common interest we share. The Straight Woman is hella sexy, possibly my age, educated, sophisticated, accomplished in her own way, and for those of you who this matters for, she’s Black. Now I can admit that I have developed feelings for The Straight Woman and based on the conversations she has initiated (topics, etc) something about me intrigues her too. I haven’t asked her about her orientation, and truthfully I’m not sure I know how to do so.

This has never happened to me before, I used to be a serial monogamist and when I was interested in one woman she was my focus. I never dated or entertained more than one woman at a time, but my oh my have the tables turned. I love being chased by The Cougar, she’s very charismatic in her approach but realistically I don’t think I can speak or act on my feelings for The Straight Woman. I’ve never been one to pursue a woman who was not already a Lesbian and part of me doesn’t want the proverbial headache that comes along with acclimating someone to a Lesbian relationship, but then another part of me thinks being open to turning a woman who is straddling the proverbial fence out because hey we all gotta learn from someone, right?

The last thing I want is to get caught up in a Trey Songz "Last Time" situation...Now that is a true Dilemma...