Ask Carolyn: How Long Should I Wait, Batting for the Other Team & More

sex questions, love advice, relationship advice, how long should i wait before sleeping with someone, am i bi-sexual, should i tell my ex i'm dating
America’s favorite divorced, single mother!

Hello friends! We’re back with another installment of Ask Carolyn, Your Sex, Love and Relationships “Ex”-pert! I’m America’s favorite divorced, single mother! If you aren’t familiar with what this column is about, read the first installment here. If you are, let’s do this thing!

This week readers wanted to know how long to wait before sleeping with someone you’re dating, how to try batting for the other team and if/when to let your ex-spouse know you’re dating someone. Here are my thoughts:

From Jeni: How long should I wait before doing it with a date?

As a 37-year-old woman living in NYC, what is a reasonable amount of time I should wait to sleep with someone new? Asking for a friend of a friend’s mom.

My fellow single mom friend, Bonnie, responded on Facebook:

30 minutes. Or less. Or maybe that’s just me.

Jeni, I’m so glad you asked, because this is something I’m trying to figure out myself. (Bonnie – listen up.) I had a couple (literally two) one-night-stands after I got divorced just to kind of get back in the game, and then I had this tawdry mostly sexual relationship with a guy I fell for hard (no pun intended, but that was at least half his allure), and then I finally said to myself, okay, no more of this business. If you want to find a nice guy, you have to go out on proper dates. I went out on four proper dates with a very nice guy after that, and we slept together on the fourth and final date. We didn’t go all the way (as the kids say … back in 1954), but we did mess around, and I knew then that the chemistry wasn’t quite right.

I think the key to knowing when to sleep with someone you’re dating is to be really, really honest with yourself about what your gut is telling you about your connection with the person. If you think, okay wow — this person is really blowing me away and I feel like we could have a serious relationship, wait as long as you can. And talk to the person you’re dating. Say something like, “God, I like you so much I totally want to sleep with you but I also don’t want to ruin it.” Then ask him how he feels. If you’re just casually dating someone for fun and you’re mostly looking for a steady, monogamous sex partner but not necessarily something super long-term, be honest about that, too. Most guys will be cool with that kind of relationship. And if he ends up really liking you as a result of that relationship and he wants more, you can deal with that when it comes up. Chances are your feelings might change, too. Sex is powerful that way! It bonds people, like it or not, so before you have sex with anyone, make sure you’re willing to be bonded to them in some way even for one night.

From David: Break on through to the other side?

I’ve always identified as a gay man, but I’ve been really curious to eat a pink taco. How should I go about doing this?

Jeni responded on Facebook:

Carefully and slowly. Don’t be afraid to make a mess and use lots of hot sauce.

Yes, David, in terms of technique, Jeni’s advice is spot on. But how are you going to buy this taco? That’s the question. (No, don’t buy it. You’ll get arrested.) What I mean is, how do you choose which restaurant to dine in? How are you going to find your first opposite sex partner? I think you should pick a friend you’ve always had a fun, flirty chemistry with and just tell her, “Look. This is something I’ve been thinking about for a while. Are you interested in going out for a drink and taking it from there?” If she trusts you, she will probably say yes. That way, there’s no real pressure to MAKE IT HAPPEN and you guys know you’ll have a good time even if it doesn’t happen. If it doesn’t happen, try again with another friend, or maybe just accept that it was never meant to be! Unless you’re really bound and determined to make it happen, then you could always go to a swingers party. Unbind yourself first, though. You’re going to need your hands.

From Joseph: Do I have to tell my ex-wife that I’m seeing someone?

What is the etiquette regarding telling or not telling your ex-wife when you are dating someone? Our daughter, who is 16, thinks I should tell her mother I’m dating someone. My 25-year-old daughter, who has a different mother, thinks my dating life is none of my ex’s business. My ex-wife ran into my date yesterday at my house. My 16-year-old told her mom that my date was a friend of her older sister.

Joe! What is happening at your house, buddy? First of all, I can’t help but notice how many women are in or have been in (and out of) your life. Wow. Secondly, did you not immediately fess up when your daughter lied on your behalf? And why does your daughter feel the need to lie on your behalf? It seems from my perspective that your 16-year-old feels like she has to protect you, but she isn’t entirely comfortable doing so, nor should she be. Ultimately, if your daughter would be more comfortable if you had a talk with your ex-wife about your dating situation, I definitely think it’s your responsibility to bite the bullet here. You don’t have to go into any detail, but you do need to say, “I’m dating so-and-so, she may be spending some time around our daughter. I’d like the two of you two meet briefly to say hello.” And you should certainly apologize to your ex-wife for not explaining the situation when she ran into your girlfriend, unbeknownst to her. Finally, how young is your girlfriend if she passes for the friend of your 25-year-old? Maybe age-appropriate dating will help you with age-appropriate behavior overall? Just a thought. I wish you — and your daughters — the best!

Thanks so much for your questions, everyone! You can leave a question in the comments below or ask me a question on Facebook. Feel free to message me if you’d like your question to be answered anonymously! I’m happy to change your name or not use a name at all. Check back next Thursday for another Q & A with me, your girl CKC!


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