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How Soon Can I Have Sex with a New Guy?

“Dear Walker,

I’ve just met this great guy online. We’ve been emailing and talking for 2 weeks and now we’re talking about setting up our first date. I’m 52, newly divorced and a little nervous about having sex with someone other than my husband after all these years—but excited! Is there anything wrong with me thinking about having sex with him?




It’s not my place to tell you it’s right or wrong to have sex. You’re an adult and can do whatever feels comfortable for you. I will however offer a few thoughts about having sex the first time with a new partner.

You’re smart to start thinking about sex and planning for it. However, don’t get so excited about sex that you forget about practical matters.

When to Have Sex the First Time with a New Partner

Here are a few questions to consider as you think about having sex with this guy:

What am I you looking for in dating? Do I want casual sex or something more long lasting?

If you’re just interested in having sex then other issues of compatibility aren’t as important. If you want to find someone to date on an ongoing basis then you might want to get to know him before rushing into sex. Why? Because sexual chemistry can mask the lack of  compatibility in other areas. It’s awkward to start having sex early on then discover after a few dates that you really don’t have much in common.

Am I ready to have sex with someone new?

Having sex with a new guy involves getting naked, literally and figuratively. Are you comfortable going there? Do you have any fears or concerns around sex, how your body looks, or inviting a relative stranger into your house? If the answer is yes, it’s a good idea to discuss concerns with a prospective partner early in the relationship—which would mean over drinks on that first date.

Do I need birth control or protection?

If you still need birth control, have you talked to your gynecologist? What do you know about sexual transmitted infections, STIs? Will you feel comfortable asking him to wear a condom? And supplying him with a condom if he says no? Have you been tested to make sure you are free of STIs and HIV ?

Have safe is this guy?

If you’re going to have sex on the first date you should be very sure this man is who he says he is, where you will be meeting, and other details before getting intimate with a relative stranger. For example-his place or yours? Do anyone know where you’ll be?

First date sex can be breathtaking and exciting. And if that’s what you want and you feel safe then by all means go for it. Just make sure you feel absolutely comfortable with this person. And, have an initial conversation about sex and your expectations. If you have any challenges, limitations or concerns share them with your date. Talking about sex will give a feel for what kind of lover he is. What do your instincts tell you about his skill and his approach to sex? Is it compatible with what you want? If the idea of discussing sex seems too personal then perhaps you’re not ready to have sex?

I suggest that you think about things you want to say, before you’re standing naked by the bed. You may not actually say all of these things, but the exercise can help you determine what’s important to you.

I know I’ve given you lots of questions but it’s the best way for you to look at what you want and to be realistic about approaching sex with this guy. Being single in midlife can be exciting, scary, confusing and exhilarating. This is your time—time for you to speak up about what you want. Time to have fun!

It’s important that you date men who respect you and want to please you—in and out of bed. Don’t feel pressured to have sex too soon if you’re not ready. If you are ready don’t let others tell you when you ‘should’ have sex. After all, you are a grown woman with wants and needs! Be safe and have fun.

Ps: You might read my last article about online dating and safety.

midlife boulevard, columnist, midlife women, middle-age, midlife crisis


Walker Thornton

We are delighted to have Walker Thornton as our Women’s Sexual Health columnist. After working for over 10 years in the field of sexual violence against women, Walker is now enjoying a new career as a freelance writer, public speaker, and sex educator with an emphasis on midlife women. Her blog, was ranked #5 by in their top 100 Sex Blogging Superheroes of 2014. You can connect with her on Facebook and Twitter For questions about sexual health, write her at

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