The Right Moment

*  I’ve been friends with this woman since the beginning of the school year.  We share a large apartment with three other people and the five of us hang out together socially as well as being roommates.  I would like to get next to her on a more romantic basis.  How do I get from here to there?

Carefully, if at all.  There are several things not in your favor.  First, most people try to avoid a romantic entanglement that will make things awkward for themselves and others if it does not work out and they still have to see each other on a daily basis.  That’s one of the reasons for such as expressions as “Don’t dip your pen in company ink” or “Don’t get your meat where you get your bread”. Secondly, being seen as a possible romantic partner is often a very big chasm to leap if she sees you only as a friend.  Spend as much time with the object of your affection as you can, alone if possible, and suss out the possibilities.  Does she seem to seek you out too, or avoid being alone with you?  Is she interested in someone else?  Do you have a backup living situation available if things become uncomfortable? Think this through before making any potentially embarrassing moves.

*  I am a woman in my forties trying Internet dating for the first time at the insistence of my friends.  It seems like most of the men I meet want sex far too soon for me.  Surely not all men want sex on the first few dates, do they?  And how do I say no without losing them?

Let me say right up front that you will lose some, if not many, of the men you date by saying no to sex.  That’s what these men are looking for and if you won’t provide it, why bother?  The ones who want a mate or a sweetheart or a real relationship between humans rather than their parts will put up with their frustration and hang around until you feel comfortable and ready for physical contact. It may seem that men you meet online are more sexually aggressive and that might be so.  They won’t have to face you in every day life knowing that they acted like bores.  The Internet allows for meeting more people but it also allows for some of them to behave badly with fewer consequences. The more you practice saying no, the easier it will become.

*  The idea of oral sex squicks me out.  Putting my mouth where someone else pees and may not wipe carefully or at all, does not sound sexy to me.  Do I have to do it?

Do you think you’ll be sent to your room without dinner if you don’t?  There’s no “have tos” when it comes to personal pleasure, which is what sex is about – your pleasure as well as the pleasure of your partner(s).  So the real question is does your partner require this kind of stimulation and, if so, then what? Many men and women see oral sex as a natural and necessary part of loving sexual expression and would find your distaste disappointing, to say the least.  Is it a deal breaker?  Only your partner can say.  I suspect your question is theoretical.  If and when you find someone whose body you can’t wait to explore, you may feel  differently.  Bathing or showering together before being physically intimate is a fun thing to do and can eliminate some of your worries about genital cleanliness.