The V-Spot: Who Do I Choose?

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I’m a 61-year-old woman dating two men. One of them is a retired, 75-year-old secure man who knows who he is. The other is in his 50s and is still trying to figure it all out. Neither of them knows about the other one and live at a distance from each other. I just ended a 35 year marriage and don’t want to be in a committed relationship right now. I love parts of both of them and I love what both of them bring to the table. Who do I choose? I don’t want to stop dating either of them. I guess I’m just seeking validation that it’s okay to date two men at once.

I can only imagine how dating practices, taboos and norms have changed in your 61 years. They’ve changed so much just in my 30! With the advent and availability of everything from the birth control pill to Tinder, the way we date, fall in love, have sex, and find people to do all of those wonderful things with has evolved at a rapid clip. 

The most meaningful validation will come from within yourself, TBT. You sound happy and fulfilled so let’s shut down these mass messages that say dating two men at once is wrong, slutty, or shameful while a man doing this with two women makes him cool, powerful, or otherwise player-esque. 

Secondly, in the 35 years since you got married and took a hiatus from playing the field, the rules of the game have changed. Casual sex, casual dating, and dating two people simultaneously is getting less risque by the minute. Buzzwords like “polyamory” and “open relationship” are flying around everywhere from books (see Opening Up by Tristan Taormino), reality TV shows, and even workshops, some of which are taught by yours truly.

At a recent workshop I met two participants in their 60s, one of whom had been practicing non-monogamy — the practice of dating more than one person simultaneously — for over 40 years. He described a long journey of being closeted about his multitudinous love life and relief at today’s more open dating culture. Long story short, you’re certainly not the only person in their 60s looking beyond monogamy. 

You mention that neither man knows about the other. I’m assuming that one of your hesitations about dating both is you feel as though you’re cheating, keeping secrets, or otherwise being dishonest with them. One of the key components of ethical non-monogamy that separates it from cheating is being open with your partners about the fact that you’re dating other people. This prevents hurt feelings if either man is assuming you are monogamous with them or want to be, and gives them the choice they are entitled to, to continue to date you non-monogamously or end things.

But perhaps you’re not there yet. If you’ve just started dating these men casually, it may be time to have what the Tumblr tots are calling “DTR” – or the “Define the Relationship” talk where you sit down with each man and say, “Okay, what are we doing here? Are we keeping it casual? Just having sex? Getting serious?” This is also a great time to state your desires and boundaries such as, “I don’t want a relationship right now. I’ve been dating this other man and want to continue to do so, etc.” This way everyone involved can state what they want, get their questions answered, and make sure everyone’s on the same page to help prevent hurt feelings or perpetuate secrets.

So, who do you choose, TBT? Choose yourself! Set your boundaries and your desires, and follow what makes you the happiest. Just make sure to clearly communicate with those you date about the parts of your love life that directly affect them.•

Yana Tallon-Hicks is a pleasure-positive writer and educator living in the Pioneer Valley. She has a website bursting with sex advice, resources, and workshops at yanatallonhicks.com.

Yana Tallon-Hicks

Author: Yana Tallon-Hicks

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