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Are his actions Red Flags? He's a confident guy but insecure with me

Tagged as: Dating, Trust issues<< Previous question   Next question >>
Question - (2 June 2016) 3 Answers - (Newest, 4 June 2016)
A female United States age 30-35, anonymous writes:

I've been dating a great guy (31 y/o) for two months. He treats me very well, initiates most dates and text greetings, and invites me to his friend/group gatherings.

He's a successful entrepreneur, experienced, outgoing, and very socially capable (a great networker). So far we seem to be a great match, but I would like some input on his behavior. For context, he's not my boyfriend (yet).

I’ll try to condense.

First, he rarely makes eye contact with me and when I mentioned once he said he’s never been great at eye contact. When he catches me looking at him he’ll blush/smile and look down. I asked if my looking makes him uncomfortable and he said “yes.” Which is fine. If that’s just how he is, I can accept it. BUT he does make eye contact with everyone else including friends and strangers. This makes me uncomfortable because it’s just ME.

Second, during our first whole month of dating, he never asked me out directly. It was always "hopefully we can hang out again" or "maybe hangout later?" Even though I never initiated during that first month, I always reciprocated well and suggested plans right away.

Third, he's always the little spoon. Whenever we sleep, he always wants to be held. Whenever we hang out on the couch, he lays his head on my lap. And when we're out with friends he likes leaning into me too, sometimes resting his head on my shoulder.

Lastly, recently I was texting someone in front of him (we both do it from time to time) and he abruptly leaned onto my shoulder to see my phone. He’s never done that before and it caught me off guard so I flipped my phone over. He didn’t even try to be subtle.

Later that same day, we ended our date earlier than usual because he had a concert to attend (tickets bought way in advance). I remember that day he asked me three times what my evening plans were, and each time I said nothing planned so probably just going to go home. Anyway, before he left, he sprayed a ton of cologne then gave me a big hug right after which came off as oddly intentional. He said he’ll call me if the concert doesn’t end too late but he never called. But I think we both already knew the concert would end late.

I don't have a problem with any of his above actions (except maybe his abrupt phone peeking) but I’m getting the impression that he’s insecure with me. He seems very confident with friends, strangers, and clients, so I’m wondering if I’m making him uncomfortable. My weakness is that I rarely initiate and share my feelings so perhaps he cannot tell what I’m thinking. But I should also mention that he’s been cheated on twice before.

His last relationship ended 5-6 years ago and lasted 7 years. I know he’s afraid and we agreed to take things slowly for the both of us (physically as well). We are not exclusive yet.

What do you all think? Any red flags I cannot see, or am I just over thinking? Is either of us doing something wrong we cannot pinpoint?

I am new to the adult dating world so any advice would be greatly appreciated. Thank you.

View related questions: insecure, text

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A female reader, singinbluebird United States +, writes (4 June 2016):

singinbluebird agony auntI know many men like that. Sounds like he's not necessarily insecure but more like unsure and shy because he really likes you. Also he sounds like a talker and a emotional man, possibly great communicator and loves sharing what he has and his life with everyone. You really do have a catch but heres what youre pinpointing at --- he's slightly effeminate (or feminine). Theres nothing wrong with that. Its even sexy in some men

There are no red flags but he will be himself and if you like him, I dont think you should be concerned at all.Men who like to be the small spoon are probably confident but enjoy being safe and held when in the prescense of what they sense is a confident beautiful woman (hence lying in your arms and youre not lying in his). Its a weird feeling but forget about gender roles for now. If you like him take him up on it. Learn what you both enjoy and do what you love while with him.

If you want to be the small spoon or make him more confident, when cuddling immediately lay in his arms and cuddle.

Tell him you enjoy it when a guy takes control a bit (say that it turns you on) or gently pushed him towards it but not in criticizing way.

Good luck

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A male reader, Garbo United States +, writes (3 June 2016):

Garbo agony auntI see no red flags in any of this. Perhaps he wants to hear from you that you are interested in being exclusive and willing to offer commitment so you may want to discuss that with him as a possibility. So if if you see future with him, start sharing some of those thoughts with him. As for eye contact, people with Aspergers never look in the eyes although sometimes they learn to in business situations where they have to. Then again, it could be a learned behavior because some people stare at lips instead.

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A female reader, Honeypie United States +, writes (2 June 2016):

Honeypie agony auntI don't see any red flags from what you describe. I think not looking you in the eye is a little odd, but it can be chalked up to be a little shy around you. And that can be because he REALLY likes you.

Putting on cologne before going out seems normal to me. Most people who are going out, whether it's to a concert, dinner with friend, family, the movies or whatnot, wants to look and smell good. So nothing odd there, IMHO

If he hasn't dated in a long time, maybe that is why he sticks to the more vague approach, he is simply out of practice. OR he is trying to get YOU to show more interest. So a "general" let's hang out again soon might be him tossing the ball in your court.

My advice, keep going slow. But do open up a little and if you really like him, try and meat him halfway, don't make HIM the only one to plan stuff. So work on your 'weakness" and take some initiative.

I don't think you two are doing anything "wrong" per se, but if the past is still lingering (as in fear of getting hurt again being cheated on, etc.) you are both holding yourself back from properly investing in the relationship. Which CAN mean it's over before it even begins.

Living in fear of the past repeating itself is going to cause you regret for not living life to the fullest. Both of you.

Be honest with him, hopefully he will be honest with you too.

Nothing ventured, nothing gained.

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