I'm at the risk of becoming a 40-Year Old Virgin in a few years. My dating history is non-existant, and even in date settings I have issues with intimacy. I'm scared of the potential for pain in sex, and that is something that will be off the table for me if a relationship were to start. For my age group, I know its pretty much common for men to have experience, and I'm going to want to take it slow given my lack of experience. What's the best way to approach this, and is this something I should have on my dating profile?
First, please know that sex is merely an act, something people perform for a variety of reasons. It's doesn't define us or what constitutes a relationship. Plenty of people have healthy romantic relationships that don't involve sex.
If you do wish to engage in a sexual relationship but feel something is holding you back, I would urge you to research and find a good therapist, one you trust, as well as a gynecologist. The former would be to investigate your ambivalence and see if it's rooted in trauma or not. The latter would be to discuss if there are any physical issues at play that might cause you discomfort during sex. Note that you don't have to have experience trauma to have a low or non-existent sex drive. I really dislike the idea that a woman who doesn't enjoy or frequently engage in sex must have some kind of trauma in her past. It's an uninformed trope.
If it's the potential for physical pain is what's keeping you from having sex, there's something you can do about that in the privacy of your own home. There are all kind of pleasure-seeking devices out there for women to use. We grow up with so much shame around sex that often times we feel too embarrassed to explore our bodies or what we like. Women aren't usually encouraged to do that. What ends up happening is we have sex for the first time and it is either extremely uncomfortable or totally dissatisfying. As a result, we assume that's normal or just what sex is and proceed to develop a disdain for it altogether. Those early experiences sully our future sexual selves.
Please keep in mind that it very well might be that you just don't have an interest in sex and that is a valid and common orientation. Asexuality doesn't mean you don't experience physical attraction. It simply means that you don't feel compelled to express that attraction through sexual activity or intercourse. There are asexual (or "ace") dating sites out there you might want to check out.
Now, let's talk about your dating profile and any potential conversations that might arise.
First, leave this information out of your profile. You don't owe internet strangers or even people you message with any explanation as to why you will or won't be sleeping with them. There's no need for full disclosure upfront. You're not a commodity or something being sold. You're a human being, and human beings usually come with a complex set of experiences. Those conversations - and any conversations where you divulge sensitive or deeply personal info - are for people who have earned the right to hear them. Your story is your story. Everybody has one.
The other reason to keep from mentioning this in a profile is that you will make yourself vulnerable to the wrong people. Here's a list of things you do not want to mention in your profile:
Past physical or sexual trauma
Recent romantic upheaval (break-up/divorce) - Grief isn't just an emotion or process we experience after death. Grief is common when we lose anything of significance - a job, a relationship, money, etc. A smart fraud knows that trauma affects people's judgment and will use that to their advantage.
Physical or mental illnesses - As someone with depression, let me make it clear that I'm not suggesting you keep this to yourself due to any stigma. Rather, I don't want the wrong person to see that and try to exploit what they perceive is a weakness.
Being a widow/widower - An admission likes this plants seeds of doubt in people's minds about your readiness to move on. It also lends to the impression that you're grieving and lonely, which makes you vulnerable to those looking to scam you.
Being new in town - It's critical that you make clear that you have a support system - friends or family online or off - that has your best interests in mind. That's going to dramatically lower your chances of being targeted by a scammer. Scammers want people who are isolated because they're easier to manipulate and coerce.
Being financially secure - Many women feel they have to prove they aren't looking for someone to take care of them. Many men that include info to imply they can support someone. Either way, you're painting a target on your back. Grifters, con-men and other deadbeats will see that and swoop in.
Dating frustration of any kind - Someone with bad intentions will assume you're rip for the picking. They assume all they have to do to get what they want is sweep you off your feet.