How Soon is Too Soon to Have Sex?

People write in to ASK MIDLIFE BACHELOR with questions.  An index of all Q&As is located on the ASK MIDLIFE BACHELOR INDEX page. Email your question in complete confidence to [email protected].


I met a 37 year old man online. He has never been married; no kids. He lives about 1.5 hours away in the country; I live in the city. We have talked on the phone, emailed and met in person 3 times over the last 6 or so weeks. The three times we met were when he was in the city and the circumstances have been such that regular dates have not happened.

During our first telephone conversation he asked directly if I liked sex. I replied honestly that I did (cuz I do). He apologized for his direct question but explained that his past relationships each involved a woman that did not like sex. It seemed this was important to him and I told him that I agreed sex is important in a relationship.

After that there has been a sexual undertone to our conversations. The first time we met we simply talked and absolutely nothing physical happened. He admitted later he wanted to kiss me that night but refrained so as not to scare me away. The second time circumstances were such that I ended up inviting him over to my house. I have never invited a guy I met online to my house but my intuition was that I could trust him. We talked, cuddled and made out. I surprised myself with how far I went and how far I was willing to go with him. He was the one to stop things so that I wouldn’t get the wrong idea. I have


never gone so far physically with someone I didn’t know very well so I wondered how this would affect things. I worried how he would perceive me.

Conversations after this night became more sexually charged than before. The third “date” recently occurred and we ended up having sex. He called the next day, which made me feel better about things, but I wonder where things go from here.

A further complicating factor is we are both still online. I have never met anyone online I wanted to date more than twice let alone wanted to be intimate with or date exclusively. I’m concerned that things may have gone too fast such that if I have a “talk” with him about where we are at it will scare him off. I do not want to be intimate with him and continue to meet other guys and I don’t want him to meet other girls while he’s intimate with me. I would also like to slow things down a bit so that we can get to know each other a little more and so the relationship isn’t 100% sexual.

If I ask him to delete his profile (and I would do the same) in order to continue forward with me, am I asking for too much too fast? Should I talk to him about going on regular dates (i.e. out in public) and my reasoning behind it or simply insist on regular dates when we plan to get together (which could be viewed as game playing, which I hate doing)?

MIDLIFE BACHELOR ANSWER:  Thanks for writing in. I, personally, do not believe there is absolutely anything wrong with focking someone on the third date (even if all three dates were not necessarily real “dates”). We men appreciate this – we have something called “the three date rule” which means you should know where the relationship is headed by the end of the third date. [There is better explanation of The Three Date Rule here located in the Midlife Dating Advice section under Develop a Strategy for Midlife Bachelor Success.] So do not feel bad – no reason to at all!  It is a matter of efficiency. He is a lucky man!  Remember, from what he said, his last two girlfriends were not into sex … so you probably pumped up his ego quite a bit, I would imagine.

In terms of asking him to delete his online dating profile, and not see other women … if that is what you feel is right in your heart, then that is exactly what you should tell him. And if he then tells you to take a leap, then that means fate did not want this relationship to continue. You have to follow your heart – and do what is right for yourself … that is what’s called “being true to yourself“. And it is not a game, it is what is real. Besides – if he won’t do what you ask, then he is just a player who is out to get everything he can. [Nothing wrong with that either … that would just be in a different place than where you are.]

Regardless of whether this relationship works out or not – I definitely think it was a good experience for you. You went outside of your comfort zone with this man. You are the one who has to decide if the experience was good for you or not – and what you learned from it. I think it is good for everyone to get outside of their comfort zone at least once in a while … that’s one way to grow as a person.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.