Hey,
I'm unsure of what to do in this situation, I can't believe I'm almost 40 and still not sure how to deal with the opposite sex.
I got out of a very long term relationship almost 2 years ago and have worked on myself ever since. I've tackled my weight and spoken to a therapist dealing with my low self esteem and generally my confidence has boosted.
I'm middle management with a handful of team leaders underneath me, it's a very fun environment and I love my job..... now to my issue.
Myself and 3 colleagues (2 of which are in a long term relationship) decided to go out for a couple of drinks after working late on a Friday night. I had a hotel room booked at the pub and met them downstairs for a couple of drinks. An hour or so in the couple decide to head home, leaving myself and my male team leader in the bar. We have 3 more drinks nd the bar closes. I suggested that if he wanted another drink then I had a bottle in my room. He accepted me offer and as you can guess, one thing lead to another and we slept together. I've fancied him for months and his flirtiness lead me to think he may have fancied me too. He left before I woke up (he was back in the office early the next day).
Now, I see him on the Monday and it's a little awkward but nothing bad. But nothing is mentioned about the Friday night. It's now 2 weeks later and neither of us have discussed that night, other than when another colleague asked how the bar was that night and I said in front of him "I had a really fun evening".
After the first couple of days he reverted back to his usual very flirty self, even calling me the little nickname that he was calling me before we slept together. We are both single and he is leaving the company at the end of the month. I really want to ask him out but have I missed my boat? As you can tell I'm usually very shy and I'm very rusty in the dating game after a 15 year relationship.