These will be self-evident – you won’t need to pull out your magnifying glass, start making things up or coming up with rationalisations. Whether it’s figuring out what’s going on in a troubling relationship, understanding you and self-care, or being more assertive, I’m here to help you guide you. As long as he knows that his advances will be well-received, he will probably make the advance.
I get so many emails asking me about whether to date someone who is separated, recently divorced, or even fresh out of a breakup that I wanted to tackle this tricky subject.We’re often scared (even if nothing has actually happened yet with a particular person) that we may be letting our last chance or even best chance saloon slip away.We may be imagining all sorts of problems that may or may not exist or we’re rationalising our own boundaries, values, and even prior experiences of being in one of these situations (so knowing that we may struggle with the emotional consequences) and are thinking along the lines of, ‘Well…I’m of a certain age so I need to prepare myself for turning a blind eye to any code amber / red actions and indications because people in this age group tend to be recently broken up / separated / divorced‘. There’s no easy answer to the question of what the ‘right time’ is for dating a separated or recently divorced person." If you answer these questions sincerely and still want to date him, you then face the problem of making it happen - or rather, making him make it happen. They fall outside of the predator-prey model for sexual interactions that is assumed in the "don't initiate contact" rule.
So it is acceptable for you to initiate with a shy guy. The problem with male shyness is that it wears off in specific situations.What we forget is that even if a person hasn’t just exited a relationship, aside from knowing our own boundaries (which can rule out certain things that we’ve already made a decision on in advance of), we cannot get all of the answers upfront or have someone tell us what ‘the ending’ will be.Each situation is different but what you can say with a high degree of certainty is that someone who’s just fallen out of their marriage, who’s still in reconciliation negotiations, who’s still very influenced by their spouse, and who has been separated for a long time ‘just because’, is going to bring pain into your life.Same goes for someone who’s not over their divorce and has beliefs that affect their ability to be committed.I personally know people who have gotten together while one party was separated, and in one case the wife refused to sign so they had to wait for it to lapse and got married as soon as it did a few years later, and in the other instances where it worked out, there was no faffing about with the divorce, Future Faking etc.We can take the period of time since the breakup into account but we also need to note whether actions matching words are amounting to somebody who is available for a mutual, consistent, balanced (no pedestals / controlling), progressing relationship that can blossom into increasing intimacy and commitment. It’s very easy to look at a person’s age, background, what they earn, their relationship history, their appearance, their divorce, and whatever else we’re focusing on, and rule them in or out on this basis, but in the end, regardless of any of these things, we still have to assess our own boundaries and do the due diligence. If you typically struggle with the uncertainty that comes with being with somebody who still has their previous relationship to resolve, or you know based on experience that you’ve had your fingers burned by being involved with separated or recently broken up people, don’t go there.