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To browse questions by day in September, 2013, use the links below (in brackets, number of questions on that day in this category)

2 (1), 8 (2), 11 (1), 16 (2), 18 (1), 22 (1), 23 (1), 26 (2), 28 (1), 30 (2),

Archived questions from: September, 2013 (see latest in Age differences category)

Age differences: Help and advice

Any advice on regaining some sort of power in a casual relationship?

This question has 13 answers - newest was posted 4068 days ago

30 September 2013 (F) - Hi, I find myself in a bad situation, the classic casual hook up turned messy. I am seeing a younger man casually (I didnt think there was a future in it because of the age difference) and now I am having the usual problems associated with ...

Did he see this as a one-night thing?

This question has 3 answers - newest was posted 4069 days ago

30 September 2013 (F) - I have a complicated situation. A week ago, I met a guy while out, and we ended up hanging out all night (just hanging out). I am 31, and I found out later that he is only 21!!! He is not your typical 21 year old at all, more mature, lives on his ...

Why did my 30 years older than me coworker talk to me about his wife and kids?

This question has 4 answers - newest was posted 4071 days ago

28 September 2013 (F) - I don't understand why we had this conversation?what do you think the meaning was. through work i've come across a worker who now i am involved with for some work. first time saw him he shook my hand and when leaving patted my back. Thats fi...

She flaked on me then said she was sick. I haven't heard from her for 2 days.

This question has 2 answers - newest was posted 2142 days ago

26 September 2013 (F) - Ok, so I am friends with this woman, we have been acquaintances for a while but really only got to know one another out of work the past 6 months or so. I'm the mean time she's gone through a break up with her ex and a lot of stuff - fair dos. ...

How do I let him know I'm interested without embarrassing either of us?

This question has 7 answers - newest was posted 4069 days ago

26 September 2013 (F) - Hey I'm a 17 year old girl and I really like someone aged 25. I understand that we're at different points in our lives and I may be a bit young for him at the moment but we really connect and get each other really well. I feel he's hinting at ...

Is he cheating or just really busy?

This question has 5 answers - newest was posted 4076 days ago

23 September 2013 (F) - Hello ok I had met this guy who is younger than I am, he is 31, I am 40. He seems like a nice guy and we would talk on the phone pretty much every day. He also kept bugging me about when I would take the Greyhound to meet him. I kept putting it off ...

She doesn't want to lose our relationship but she doesn't want to fully commit either

This question has 9 answers - newest was posted 3938 days ago

22 September 2013 (M) - My girlfriend and I have been together for about three years. She is 19 years younger than me. I am a young 65. During this time she has lived with me at my flat although she has her own cottage in a nearby town. Recently she has talked about, '...

Can an affair with a married man ever end happily for the other woman?

This question has 52 answers - newest was posted 4072 days ago

18 September 2013 (?) - Hello everyone. Before I begin, I realize I am opening myself up to a firestorm of very harsh judgment, name calling and comments from Dear Cupid's advice givers and readers. Please do not judge me. We all walk different paths in life and make...

Should I date this older woman?

This question has 9 answers - newest was posted 4082 days ago

16 September 2013 (M) - Dear all, I am really torn about this and need some objective advice (besides I am too ashamed to ask any of my friends). I will start with a quick summary about myself: I am 30 years old and had only had one relationship in my whole life. I...

Why is she so quiet and boring?

This question has 11 answers - newest was posted 4083 days ago

16 September 2013 (M) - I recently met a beautiful girl that's 10 years younger. Physically, she's perfect but she is extremely quiet on dates. It's very awkward as we never engage in conversations. We can go 2-3 hours without saying much to eachother. I try to sometimes ...

My friends and family are judging me for having a relationship with a man who is my mother's age

This question has 8 answers - newest was posted 4087 days ago

11 September 2013 (F) - I'm in a relationship with a man that is much older than me. I just turned 18 and I recently met this guy that is 37 years old. He has a son that is 2 years older than me and he is not married. I strongly believe that age is just a number. All my f...

He's 14 years younger than me, is it possible that he might like me?

This question has 9 answers - newest was posted 4090 days ago

8 September 2013 (F) - I need your advice! I am a 46 year old single woman and work with a 33 year old guy. He is nice and kind and helpful and flirtatious towards me. He is always ready to help. Although I am 46 but I look less ( I guess) specially my body looks very in ...

Is the guy I like gay?

This question has 7 answers - newest was posted 4090 days ago

8 September 2013 (F) - I think the guy I like is gay. But I don't think he even knows it yet. Don't get me wrong, I have nothing wrong with gay people, but I have this habit it finding/falling for gay guys and I would rather that not be the case with this guy. I have ...

Is it a red flag when a 55 year old man has lots of female friends young enough to be his daughters?

This question has 13 answers - newest was posted 4095 days ago

2 September 2013 (F) - Hello. I am 35yrs female (single). I am dating a guy who is 55yrs old (divorced). I like him very much and we are taking our time knowing each other. There is not intimacy between us yet and I like the way he respect it and we share quality time and...