The following advice has been updated:
- Get yourself a therapist. If you do nothing else, do this. You’ve got some issues that you need to work through — trying to resolve them on internet forums won’t work. If you’re insurance covers therapy, then you’ve got no excuse — carve out the time and commit to this. If you don’t have insurance, here are some suggestions for still getting the treatment you deserve. Additionally, read some decent, well-reviewed self help books. In short, do the hard work of self improvement.
- Just get sex over with. Johnny suggested below that people in this position get a prostitute and while we agree that sex need not be such a big deal and you should perhaps just try it with no strings attached (if you’re so inclined), a sex surrogate may be the better way to go. Surrogates take a more therapeutic approach to help clients work on their sexual issues. While anyone can call themselves a surrogate, the International Professional Surrogates Association seems to be the leader in setting guidelines and offering certification, so check out their site.
- Consider embracing celibacy. Sex can be emotionally and physically risky and complicated. Plenty of people find peace in eschewing all sexual encounters. While sex is necessary for some people, others find it a burden they prefer to live without. There’s no shame in either approach.
- Try dating. A lifetime of avoiding romantic relationships may have perhaps left you a bit socially awkward; but being charming, having a sense of humor, initiating and maintaining stimulating conversation — these are the things that are far more important in (and effective at) attracting partners than sexual experience or bodily perfection. If you can retrain yourself socially and eventually muster up the nerve to try dating (see #1, master #1), there are certainly steps you can take to avoid getting your heart (and ego) totally smashed to bits. For example, don’t try to date the youngest, hottest, most sought after single in the (real-world or online) room. Get to know the person’s values early on so you know they align with yours (i.e. they’re kind, understanding, sympathetic). Read up on how to be a good lover (SEX: How to Do Everything is a fabulous guide, if we do say so ourselves). And should sex look like it might be a possibility, give your by-then trusted partner a heads up about your concerns and (in)experience to avoid any surprises. There’s no guarantee you end up with a serious partner, but chances are you won’t experience true naked devastation in the bedroom.