I’m 20, going into second year University. I’ve never had a steady boyfriend and I also haven’t ever had sex.

There was a guy at school who said he wanted to have sex with me and I turned him down.

But now we’re both working at summer jobs, and he’s contacted me to hang out together.

I know he just wants sex, but I’m thinking maybe I should just go for it. I don’t want to stay a virgin. I’m scared that if I keep resisting until Mr. Right comes along, it could be years!

Can a person have sex just to find out what it’s all about without getting a terrible reputation? Or, feeling like scum after?

Considering the Leap

How this “leap” works out depends on whom you choose. If this guy is selfish, and just wants to satisfy himself, you’re going to feel used and crummy.

The best introduction to sex is with someone you like and respect as a person, and are likely to see again both in a friendly as well as sexual way.

But there are other considerations even for a one-off encounter: Is he someone whom you can trust won’t be brutish, or talk about you as if you’re fair game for others, or treat you like a service provider when you’re having sex?

If you even suspect that this guy fits any of these negatives, you’ll regret choosing him, especially when you’re both back seeing each other at the same school.

Trust me, virginity isn’t a condition you’re stuck with for years.

However, choosing badly now could leave you with a negative feeling about yourself and about sex.

Consider all this before you decide if this guy’s okay as your choice. Then hang out together a few times, before taking the “leap,” so you can better assess your comfort level with him.

I’m 52, and widowed a couple of years ago. My husband was older than me by 20 years, but the love of my life. I miss him, and miss the great affection between us.

Sex had stopped when he got cancer, but we still expressed our love every day.

Now, a man whom I met online and have dated twice, wants a purely sexual relationship. I respect that he’s honest about it.

He’s 58, and enjoys my company a lot, but after two divorces he doesn’t want to be tied down.

I didn’t care about missing sex with my beloved husband, but now I’m aroused at the thought of having sex again. Is this a bad idea?

Weighing the Options

A sexual relationship can be physically satisfying and enjoyable IF you don’t expect more, and don’t get disappointed when it doesn’t progress.

And, IF you respect this man in other ways, not just for his (self-serving) honesty.

You need to know much more about him.

You don’t want to take a chance that he might be a player having sex with several women (raising the possibility of his carrying a sexually transmitted infection).

And you don’t want to risk exposing your private life to a potential scammer (e.g. the financial sort, who could be preying on you as a widow).

Let him know you’re not looking for a full-on relationship but won’t rush into a sexual one with a near stranger. Ask questions, and make sure you’re comfortable with his answers.

Take time to be sure you feel safe before you commit to a sex-only connection.

FEEDBACK Regarding commentary from your readers about the woman, 48, who wrote you about dating her ex-husband’s son, 25, from his second marriage, and not her step-son (May 3):

Reader – “You provided a great tip at the end of the article: “There’s more to recognize about unusual factors in a relationship than just an age difference.”

“I am 66 and my wife is about to turn 40. We have been together 12 years - the best 12 of my life.
“There is so much more to us than just the age difference.
“So thanks for publishing the article.”

Ellie – You’re welcome. It was another chance to show that people sometimes focus on the issue they can handle, and ignore those that are more problematic, e.g. a drinking problem, or, in the case of the “older” woman, the fact that the young man’s parents were her friends and she knew they’d be appalled at his dating his father’s ex-wife.