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I want to encourage him, but I don't want to be called a tease if this doesn't work out. Advice?

Tagged as: Age differences, Dating<< Previous question   Next question >>
Question - (21 January 2012) 4 Answers - (Newest, 10 February 2012)
A age 41-50, anonymous writes:

I went on a date with a guy recently. We have another date next week. I just want some advice on how to handle this as I try to feel him out.

I'm new to the city I live in and met him through a new acquaintance. I enjoyed chatting with him the first time I met him in a group, though I sensed he was a little nervous when there was a pause in the conversation. The same acquaintance invited us both to a dinner. We sat beside each other and talked some more. We all watched a movie and I gave him a ride home.

I got an email at 1AM saying he wanted to have dinner with me next week. He ended up taking me out for my 31st birthday. He was a lot more awkward on a date than in a group. He's very smart and has led a very interesting life, but there were a lot of foot-in-mouth moments.

Here's the thing, he's a lot older than me, he's 47. The age doesn't really bother me, but I get the sense that it puts him off. Also, he's a big guy, he's overweight, which isn't a problem necessarily, but I'm kind of a health nut (I used to be overweight, I hated it, and work out regularly to maintain my health and my figure) so I wonder about the potential of it.

Also, while he seems very encouraging and interested in meeting me via email, he seems a little more detached in person. I asked him a ton of questions about himself and while he seemed very open and talked a lot about himself he barely asked me anything.

I do like him. I enjoy listening to him. I don't mind it when he touches me, I don't get any creepy vibe off of him.

I also really like that he asked me out on a date and was such a gentleman about it. I think I'm a pretty attractive woman most days. I get looked/leered frequently and occasionally respectfully and sincerely complemented by strangers, but hardly anyone ever asks me out on a date, especially men in my own age bracket. Men my own age try to get your phone number and then establish a texting rapport with your before they want to talk to you face to face. I hate this. He's literally the first man who has asked me on a date in a straight-forward way in 2 years.

I emailed him thanking him for taking me out and told him him if he wanted to get dinner later on or catch a zombie movie (a genre we both like) to let me know. He's was very enthusiastic about meeting again and we have dinner next week and has invited me to a zombie viewing 3 weeks from now.

I'm not sure I even know what I'm asking. It's been such a long time since I've been on a real date. I guess I want to give him a fair chance and encourage him as he seems a little shy, but I don't want to be called a tease if I discover that this isn't going to work. This is why dating is so stressful to me. I'm not the most experienced dater and a lot of my experiences have been disappointing. Any advice?

View related questions: my ex, my figure, overweight, shy, text

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A reader, anonymous, writes (10 February 2012):

This is verified as being by the original poster of the question

Update: After several dates and a kiss, I told him tonight that I didn't feel I could date him. I told him I liked him. I had thought about it and thought it would be nice at times, but I also told him that in my past I slept with men I wasn't sure about, then I ended up feeling awkward and guilty and it destroyed whatever relationship there was. I told him I still want to spend time with him if he was okay with it. I plan to cook him dinner on Sunday.

He was driving me home when I told him. He just got quiet. When I asked him what he was thinking, he said he was fine and he'd been rejected before. When I joked he didn't have to drive me home anymore, he smiled and said, "Well you know you'll lose a few privileges."

I'm happy I was forthright with him...I'm not great at that sometimes. But I'm feeling terrible about hurting his feelings.

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A reader, anonymous, writes (22 January 2012):

This is verified as being by the original poster of the question

Thanks for reminding me of the obvious.

Like I said, I'm new to the city I live in. I don't have any close friends around to share with or get perspective about it. I'll keep doing what I'm doing and try to stop worrying.

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A male reader, Kyle007 United States +, writes (21 January 2012):

Teasing would be if you got him all turned on and then did not put out for him. Just make a sincere effort to get to know him, and relax please, for his sake and yours.

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A female reader, AuntyEm United Kingdom +, writes (21 January 2012):

AuntyEm agony aunt1. You have no way of knowing if any liason will work out after only one date (way too soon to tell)

2. You cannot start a relationship thinking it will fail like all the others...or else...it will fail.

3. Stop second guessing everything this guy does and thinks...so he didn't ask any questions about you, perhaps he felt a little intimidated.

4. He wants to see you again and has prebooked time with you so be assured that he likes you, but allow him a proper amount of time to get to know you well before you start reading too much into it.

He seems like a gentleman, so enjoy because gentlemen are hard to come by.

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