A
female
age
41-50,
anonymous
writes:When I was in undergrad 7 years ago I was partnered with one of my classmates (Tom) to do a class project. at the time I was in an unhealthy relationship and every time I went tto class I got attention from Tom. Both me and tom were attracted to each other but we were in a relationship. Although flirting was wrong that's all we did and class finished so I kept it at that and lost touch. Fast forward to graduate school I was single and I ran into tom in the hallway(turns out we went to graduate school together and we went on a date) both of us were single but at that time I had feelings for another man so I just never pursued Tom. I've had tom on social media and every two year I see him with a new gf- I can count about 5 so far - long story short I am single again I've only had two relationships (I am 31 now) but somehow life keeps bringing tom back into my sight. He messaged me randomly on favebook again - I can see he broke up with his gf . My questions is this. Should I give this guy a chance? My close friends that know me well say to focus on his behavioral pattern- they say he hasn't had a successful relatiosnhip for the last 6 years always changing gf- they always say proceed with caution. They always bring up that he seems flirtatious all the time and if he was flirting with you while he was in a relatiosnhip what do u think he will do when he is in a relatiosnhip with you.i must say they have a point but when your lonely and sexually attracted to someone it's hard not to bite at the food they are offerings- any advice?
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female
reader, Campari Milano  +, writes (26 February 2017):
The answer to this is clear: proportionally, how much do you like this guy vs how much are you prepared to get your heart broken!You are a grown woman! You haven't evn been on a date with this guy!You haven't even had sex with him!He might be terrible! You might find that it's been a sexual tension build up and you know he's not the one for you!You're talking like you're 18!Go out with him, see what happens. I guarantee there are signs way before he dumps someone.He may think you are the love of his life!What have you really got to lose, when you've already said you're attracted to him!Are you supposed to guard yourself just in case?!Where's the fun in that?!We all get hurt, and yes, it sucks! But I'd rather know, than wonder 'what if?' Wouldn't you?!
A
female
reader, fishdish +, writes (2 February 2017):
 What are you wanting out of him? A hook up? A friends with benefits? A marriage? I see nothing wrong with you seeing him to make up your own mind. These are such weak red flags in my mind. Flirting isn't great but we don't even have a good time stamp on when he was flirting. Also some people are just naturally that way, doesn't mean they intend to act on it. If you're looking for something semi serious take it slow.
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A
reader, anonymous, writes (31 January 2017): I agree with your friends as far as the fact he has had several failed relationships since you've known him.
Another red-flag is that he flirted with you while you were both in relationships. Now you're falling back on good old Tom for the sake of convenience. He's always there waiting in the back of the closet like the little black dress you don't wear that often.
Tom might be worth a few dates, but I would reserve my feelings if I were you. I don't believe in dating people for sentimental reasons; just because we go back. I need to know something about their past during the blackout-period, and if the feelings are equal to my own.
Tom also knows you flirted with him when you had a boyfriend; so how would he really trust you? He would likely judge you for it, even if it would be hypocritical.
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A
male
reader, olderthandirt  +, writes (31 January 2017):
 Reread Honeypie and follow her advice
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A
female
reader, Honeypie +, writes (31 January 2017):
 I think your friends are right. Where there is smoke there is fire.
Someone who goes through women like him, are probably not really ready or willing to have a serious relationship. At least 5 women in 6 years doesn't really seem like a guy who WANTS relationships to last. He is OK with a so-so relationship but they all have an expiration date.
And yes, flirting with someone who HAS a partner whilst HE has a partner can be iffy too, I think it comes down to how "serious" or "overtly sexual" that flirting was. If it was all in good fun (after all he knew you had someone and you knew HE had someone, so it might have been more like banter than flirting.) Also did the flirting happen in person only or over texts/calls too? If it's the flirt, I think it's rather harmless, if it's the latter... disrespectful to one's partner.
And I do think IF there was something STRONG about you two it would have happened a long time ago. What you like at 24 may not be what you NEED at 31.
Should you go on a date with him? Well, if you want to. I'd just keep sex out of the mix til you are certain one way or the other.
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