Reader Question – Making THE Move

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“Hi Shay!

HUGE fan of your site. I have a question. I’m in male in my mid-30s, recently divorced and new to the dating game again. After many years of sexual repression in my first marriage I’m having trouble making the move with a new woman from making out on the couch to leading her up to my bedroom..It’s been too long since I had to even try! Any advice???!!

Struggling to get back in the saddle“

Congratulations on getting yourself back in the dating pool! I know that is often a very big step to make for someone who has been in a long term relationship for a while (or even for some people who haven’t).

I know that “making THE move” can seem like a huge deal before you make it. Both men and women try to plan THE move out in meticulous detail – BUT I also know that sometimes all the worrying and planning can make it that much harder and awkward.
Sometimes you just have to relax and let it happen.

Sometimes it’s best to just let things take their natural course; you certainly don’t want to rush into things too soon (I know it seems weird for a sex blogger to say something like that). You’ll want to savor each moment and each sexual (or less sexual) experience with your new lover.

When I was a young teen, my dad explained to me that romantic relationships go through a series of stages: the holding hands stage, the kissing stage, the making out stage, heavy petting, sex… and then (he told me) there aren’t many more steps after that. You’ll want to make sure that you make the most of each step that you do take, instead of hurrying yourselves right to the end.

But I’m sure you really don’t need my little “sex -ed” type lecture.
What you’re looking for is tips for knowing when it’s time to make THE move and possibly how to do it, am I right?

With most lovers, typically the best approach with a new partner is not to say something like “so, after this let’s go upstairs for sex, okay?” (at least not until you are actually having sex regularly)

You’ll want to take it from making out on the couch (like you mentioned) – try some touching, try some unbuttoning, try some whispers “oh you look so hot tonight”, “oh I’m so hard”, try some slipping of hands into undergarments… pretty much try things to let her know how interested in sex you are and monitor her responses.

If she pushes your hand away as you slide it up her skirt, she’s probably not ready. If she grabs your hand and guides it into her panties, then she might be interested and you should try more.

Things may just flow smoothly into sex right there on the couch!! But if you really had your heart set on taking it to the bedroom, one of the best times to suggest it is when you are both trying not to fall off the couch as your making out/groping gets more physical.

I’m a big fan of communication in relationships, it clears up assumptions and expectations and keeps us from screwing things up too badly…
So, you might want to simply ask her if she’s ready to get sexually intimate with you. Perhaps whisper into her ear while you make out “do you want to have sex with me?” “should we have sex tonight?” “how would you feel about me fucking your brains out for the next 3 hours?” – something like that ^_~.

Even if she isn’t ready that night, all is not lost. If she’s a “normal” healthy woman, she will be ready at some point. And if she’s like me, she might even make that first move for you (or be waiting demurely for you to ask - depends on my mood).